Tag: rental property investing

Build Out Your RE Team Starting with a Five-Star Broker
Owning rental properties should not be a solo adventure. The entire experience is better when you have someone to share it with.

We recently talked about how the most important person on your real estate team is your spouse. Make sure you each understand the financial, time, and emotional commitments involved.

Isn’t that true for most things in life?

Whether it’s a project you’re working on or a vacation you’re taking, it’s better when you do it with other people.

Owning rental properties is no different.

If you’re considering your first rental property, don’t fool yourself into thinking you’ll be earning passive income.

For me, the benefits of owning rental properties significantly outweigh the downsides of being a landlord.

It’s a tradeoff that I would happily make again and again… as long as I have good help along the way.

That help starts with a real estate broker.

If you find the right broker, he will guide you in building a rental property portfolio that you’re proud of.

Let’s take a look.

Start building your team by finding the best real estate broker.

Start building out your team by finding a real estate broker (or real estate agent) who matches your style and understands your goals.

Think of your real estate broker as a concierge at a five-star hotel in a foreign country.

My wife and I went to Australia years ago. It was probably the best trip we ever took. We started in Sydney and eventually made our way up the coast to the Great Barrier Reef.

While in Sydney, we took a couple of day trips to the Hunter Valley wine region and the Blue Mountains. We climbed Harbour Bridge and saw some animals at a zoo we had never seen before.

We met some amazing people and had some wonderful meals.

All of these experiences were arranged through the concierge at our hotel.

Before we ever left Chicago, we coordinated with the hotel’s concierge. He asked us what our priorities were, sent us options to consider, answered our questions, and then made all the arrangements.

The decisions were ultimately ours, but the concierge used his expertise and what he learned about our priorities to help us make the best decisions. Importantly, he steered us away from making poor choices.

We would have been completely lost without his guidance.

Just as the concierge helped us navigate Sydney, your real estate broker will help you navigate the rental property experience.

Your broker will wear many hats in helping you find a great rental property.

During your search for a great rental property, a good broker will:
- Educate you about the market you’re investing in.
- Send you properties that match your goals.
- Tour properties with you to help identify any red flags.
- Negotiate on your behalf to ensure you get the best possible price.
- Connect you with other key members of your team.
- Steer you away from making poor choices.
These are all invaluable services that a good broker can provide.

But, you don’t just want a good broker. You want to work with the best brokers.

The best brokers will do all of things for you during the acquisition process. But, that’s just the beginning.

The best brokers have one other trait in common.

The best brokers remain a key part of your team (life?) long after the transaction has concluded.

Getting a good rental property is just step one. Keeping the property is just as, if not more, important.

We’ve talked about how owning rental properties is a long-term game. You want a broker on your team who’s in it for the long run to help you navigate challenges as they pop up.

That’s why you want a broker who is willing to help you keep that property for the long run. That might mean helping with marketing and showing your property.

More importantly, that means continuing to give you advice and tutelage as you learn to be a landlord.

For that reason, if you are going to buy a rental property, I recommend you work with a broker who also owns rental properties.

Photo by Dane Deaner on Unsplash

I recommend you find a broker who is also an investor.

There are different factors to consider when buying a rental property compared to buying a primary residence.

A property could be a great home but would be a poor rental.

When it comes to working with a broker, you want somebody on your team who has personally experienced the challenges in owning rental properties that lie ahead.

Real estate brokers who are also investors are better equipped to teach you if tenants will love or hate a certain rental apartment.

Here’s a very basic example to illustrate this point:

I use the garbage disposal in my home multiple times every day. I never really thought about it before, but the garbage disposal is a wonderful invention. I’ll go as far as to say that I love my garbage disposal.

However, in my rental properties, I refuse to install garbage disposals.

In rental properties, garbage disposals constantly break because tenants are not always careful about what they put down the drain. Each time a garbage disposal clogs or breaks, that’s a costly repair. It’s just not worth it in a rental property.

I first learned to avoid garbage disposals in my rental properties years ago from my broker.

Yes, it’s a small consideration overall. You’re not going to pass up on a wonderful property because of a garbage disposal.

But, each property you look at will have countless little elements like this that need to be considered.

A broker who is an experienced rental property investor will have a better eye for these types of things.

Find a real estate broker can help make a list of the most desirable features for renters in your market.

My wife and I have worked with the same broker in Chicago for almost a decade. He’s been a mentor and a friend. He has helped us in countless ways, including putting together a list of features we look for in every rental property.

It’s not an exhaustive list, but here are some of the most important factors we evaluate when considering rental properties in Chicago:
1. Location, location, location. In Chicago, proximity to the L and social life (coffee shops, restaurants, bars, etc.) are crucial. Most of the young professionals we rent to are still in the “going out” phase of life. They want to live in fun neighborhoods so they can enjoy themselves when they’re not working. They typically stay in our apartments for 2-3 years, oftentimes before buying a place of their own and “settling down.”
2. Taxes. Property taxes can eat away your cash flow. We have high property taxes in Chicago across the board, but taxes vary widely from neighborhood to neighborhood. I look for properties in areas that have more attractive taxes.
3. Big bedrooms. One of the most common questions I get when I do apartment showings is, “Can I fit a king size bed in here?” People love big beds these days. This can be a challenge considering Chicago’s standard 25-foot wide lot. I look for properties with a minimum bedroom size of 10 x 10.
4. Outdoor space. Young professionals want to have outdoor space, even if they never use it. When I was a renter, I always wanted an apartment with a balcony for my grill. It didn’t matter to me that I only used it a handful of times each year. Maybe having outdoor space made me feel more grown up?
5. Parking. Even though Chicago is a very public transit-friendly city, people still like having cars. Because most young professionals aren’t using their cars every day, they want to keep it safe in a dedicated parking space.
There are certainly other factors we consider, but these are some of the first things we look for thanks to the guidance of our real estate broker.

Photo by Jaye Haych on Unsplash

A good real estate broker is absolutely critical if you’re investing outside your home market.

I live in the Chicago area and own a rental property in Colorado. Everything we just talked about becomes even more important when you invest outside your home market.

In your home market, you have the benefit of relying on your daily experiences to help select the right property.

I rented apartments in Chicago for 15 years before I bought an apartment building. That gave me a huge advantage when looking for a good rental property.

I didn’t have the same level of intuitive knowledge in the Colorado market.

Even if you have personal experiences in certain out-of-state markets, your knowledge will never match that of your hometown. No matter how many times you’ve visited a place, it’s not the same as living in that place.

That’s why having a good broker on your team becomes even more critical when you’re investing out-of-state.

I’m happy to say that our real estate broker in Colorado is the best there is.

And if you ever tell him I said that, I’ll deny it and say I was hacked.

Our Colorado broker spent hours and hours educating us about the local market when we were shopping for a rental property.

Even though my wife and I had vacationed in the area for years, we didn’t know the first thing about real estate in the area.

Before we considered any specific units, we had numerous conversations with our broker about our goals and preferences. He helped us pinpoint locations and features that we had not previously through about.

I still have the pages of notes I took during these conversations, which I reviewed constantly during our search.

If you are going to shop for properties outside your home market, be sure to find a good broker first.

The most successful rental property investors have a team of professionals working with them.

It’s not an exaggeration to say that having the right people on your real estate team can make or break your investing experience.

Having a good team in place, starting with your real estate broker, will help you avoid mistakes and stay motivated so you can keep your properties long-term.

I’ve seen too many investors sell their rental properties after a couple of years because they didn’t have the right people on their team. They end up making preventable mistakes and give up because being a landlord is too hard.

Unfortunately, that means they give up their properties long before getting the benefits from cash flow, appreciation, debt pay-down, and tax advantages.

If you’re going to take on the challenge of being a landlord, you might as well hold your properties long enough to reap the benefits.

And, you should take all the help you can get along the way, beginning with a great broker.

You will not regret having a great broker on your team.

My wife and I have been incredibly fortunate to work with two top-class brokers, first in Chicago and then in Colorado.

Thinking about it now, our brokers are similar in that they have been teachers and mentors to us.

Before you start looking for your first rental property, be sure to work with a great broker. Don’t just settle for the first broker you meet with.

This may take some time. Years ago, my wife and I met with six different brokers in Chicago, who all came highly recommended.

We were patient, asked a lot of questions, and went with the person who matched our style and who we felt comfortable with. The time we took during this process was well worth it.

Like a five-star hotel concierge, our brokers have made our investing experience as smooth as possible.

Without their guidance, I highly doubt we would have bought, and still own, five properties today.

Have you worked with a real estate broker before?

What should new rental property investors be on the lookout for?

Tell us about your experience in the comments below.
July 16, 2025
Your Spouse is the Most Important Person on Your RE Team

If you’re considering your first rental property, don’t fool yourself into thinking you’ll be earning passive income.

The bottom line is owning rental properties is a job. It’s not a full-time job. It’s not even a regular, part-time job. But, it is a job.

There will be tenant issues, work orders, money spent, and tough decisions to be made like in any other business.

For me, the benefits of owning rental properties significantly outweigh the downsides of being a landlord. It’s a tradeoff that I would happily make again and again.

But, I wouldn’t be saying that if my wife wasn’t also fully committed.

Before you buy a rental property, I encourage you to talk to your spouse first. Make sure you both are on the same page.

No, you do not have to have an equal division of labor.

Yes, you each have to commit to the good and the bad that comes along with owning rental properties.

If you both can make that commitment, you have the best shot at owning your properties for a long time and reaching that ultimate goal: financial freedom.

Before building out the rest of your real estate team, get on the same page with your spouse.

Owning rental properties should not be a solo adventure. The entire experience is better when you have someone to share it with.

Isn’t that true for most things in life?

Whether it’s a project you’re working on or a vacation you’re taking, it’s better when you do it with other people.

Owning rental properties is no different.

In fact, the most successful rental property investors have a team of professionals working with them.

Having a good team in place will help you avoid mistakes and stay motivated so you can keep your properties long-term.

It’s not an exaggeration to say that having the right people on your team can make or break your investing experience.

I’ve seen too many investors sell their rental properties after a couple of years because they didn’t have the right people on their team. They end up making preventable mistakes and give up because being a landlord is too hard.

Unfortunately, that means they give up their properties long before getting the benefits from cash flow, appreciation, debt pay-down, and tax advantages.

If you’re going to take on the challenge of being a landlord, you might as well hold your properties long enough to reap the benefits.

And, you should take all the help you can get along the way.

There is plenty to say about building out your real estate team. And soon enough, we’re going to talk about the key professionals that can help you run your rental property business successfully.

But, that’s all for another day.

Before we get to any of that, we need to talk about the single most important member of your team:

Your spouse.

The same holds true whether you have a significant other, partner, girlfriend, boyfriend, or anyone else you share your life wife.

Don’t worry about analyzing the numbers and finding the perfect deal. The rest of your team came wait.

Start with your spouse.

Here’s why.

Your spouse is the single most important person on your team.

To be a successful rental property investor, your spouse needs to be on board.

Even if you are going to be the one actively running the business, you won’t get very far if your spouse is not as committed as you are.

Before anything else, the first thing you need to do is sit down with your spouse and talk about why you really want to own rental properties.

That’s because owning rental properties is all about commitment.

It’s a financial comment, a time commitment, and most of all, an emotional commitment.

With these kinds of commitments involved, it’s essential that your spouse understands the full scope of what you’re both getting into as rental property investors.

Here’s what I mean.

Photo by Rod Long on Unsplash

Owning rental properties is a financial commitment.

This one should be obvious. Owning rental properties is a major financial commitment. It takes capital to buy properties and capital to maintain them.

When you choose to invest your hard-earned money in rental properties, that means you’re not spending that money elsewhere.

That might mean sacrificing retirement savings. It could also mean having less money to spend on your dream home. Or, less money to spend on vacations.

The point is that before you make the financial commitment, your spouse needs to be on board with why you’re making these sacrifices.

I’m fortunate that my wife and I have been on the same page with our rental properties since Day 1. Neither one of us needed any convincing once we did our homework and learned what was possible.

Today, we both understand why we’re still doing it: owning rental properties speeds up our journey to financial freedom.

It took some major financial sacrifices to get here, but we made those sacrifices together.

As the most obvious example, we delayed buying our “forever home” until I was almost 40 and we already had two kids.

Instead of buying a home in a nice neighborhood to raise our kids, we used our savings to buy rental properties. We were doing something different and it was important to be committed to our plan.

It wasn’t easy to see our friends and family members buy beautiful homes in wonderful areas. We definitely noticed more than a few confused looks when we would have people over to our small apartments in the city.

At times, we both wondered whether we were making a mistake.

As it turned out, the trade-off was well worth it.

Owning rental properties is a time commitment.

Make no mistake about it, owning rental properties is a time commitment.

We’ve talked about how owning rental properties means having a job. For lawyers and professionals, this means having a second job on top of a primary job.

Even with the best team and systems in place, there’s no getting around the fact that owning rental properties will always be a time commitment.

What does the time commitment look like? What does this have to do with your spouse?

Depending on your availability and skills, the time commitment will vary from one landlord to the next.

You might be the type that heads over to the property every weekend to mow the lawn. To take it one step further, maybe you’re the type who has the skills to handle all maintenance requests yourself.

Or, you might handle all showings and tenant issues personally.

The truth is that in the beginning, many rental property investors do all of the above themselves.

Rental property investors think of this time commitment as “sweat equity.”

Sweat equity is what you contribute to your business but don’t exactly get paid for. When cash flow is tight, as it is for most beginners, we make up for it with sweat equity.

The more jobs we take on ourselves, the less we pay out to other people.

The tradeoff is that the more sweat equity you put into your properties, the less time you have to spend at home with your spouse.

If your spouse is not on board with you being away from home, it’s going to be difficult to succeed as a rental property investor.

If you have young kids, it’s even harder. When one spouse is at the rental property, the other spouse is usually alone with the kids. Anyone with kids knows which of those two jobs is harder.

For example, there have been entire weekends that I’ve spent fixing up one apartment or another.

By the way, if you’ve ever wanted to take a tour called “The World’s Worst Drywall Repairs,” I’ve got you covered.

If it’s not repairs eating up your free time, it could be analyzing new properties, doing apartment showings, meeting with contractors, or basic bookkeeping.

With all these time commitments, I’m lucky that my wife and I are on the same page when it comes to our rental property business. We split up these tasks and cover for each other when one person is busy with other responsibilities.

Yes, you can outsource these jobs. We outsource as much as we can. But, there are certain jobs that you’ll always need to, or want to, handle yourself.

Photo by Charles Forerunner on Unsplash

As just one example, we do all our showings ourselves.

Finding the right tenants is the most important job in owning rental properties. If we outsourced this particular job, we could end up with tenants who could cause us major stress for the next year.

Regardless of the recipe that works for you and your spouse, have the conversation before investing in rental properties.

Make sure you each understand the time commitment involved.

Owning rental properties is an emotional commitment.

The financial commitment and the time commitment are only the beginning.

Most of all, owning rental properties is an emotional commitment.

Without having a spouse on the same emotional wavelength as you, it will be very hard to succeed as a rental property investor.

When you own rental properties, there will be stressful times and you’ll want to lean on your spouse for support.

There will also be moments to celebrate, and you’ll want to share those moments with your spouse.

If your spouse is not on the same wavelength as you, these moments can feel very lonely. The lows can feel much lower and the highs don’t feel quite so high.

Without someone to commiserate with and celebrate with, you’ll be more likely to give up.

My wife and I have endless stories about our experiences as landlords that very few other people would truly appreciate. We can each list off the jerks we’ve rented to and the biggest headaches we’ve encountered.

We once offered a lease renewal to a tenant at her same price. She responded that she would be happy to stay for another year if we simply replaced the kitchen countertops and appliances, added an additional bedroom and built out some new closets.

Ummm, we’ll pass.

My wife and I can laugh about these moments because we’re both emotionally committed to the journey. Living through these experiences together has helped us stay the course.

Unfortunately, I’ve met a number of real estate investors over the years who tried to go it alone. I think that’s a mistake. Oftentimes, these investors don’t stay invested very long.

It’s not because they bought bad properties or had bad tenants.

The problem was they never prioritized the most important person on their real estate team.

When challenges arose, they didn’t have a spouse to lean on.

When you’re spouse is on board, investing in real estate is a rewarding challenge.

It’s all about the journey, right?

When times get tough in our real estate business, my wife and I lean on each other. When we miss out on evenings with the kids or nights out with friends, we remind each other what it’s all about.

We remind each other that we wouldn’t be where we are today if we didn’t start buying rental properties in 2018.

We both realize the commitments involved, whether it be our money, our time, or our emotions. If we weren’t in this together, there’s no way we could run our rental property business as well as we do.

Before you buy a rental property, I encourage you to talk to your spouse first. Make sure you both are on the same page.

No, you do not have to have an equal division of labor.

Yes, you each have to commit to the good and the bad that comes along with owning rental properties.

If you both can make that commitment, you have the best shot at owning your properties for a long time and reaching that ultimate goal: financial freedom.

Did you talk to your spouse before buying rental properties?

Do you run your rental property business with your spouse?

What lessons have you learned along the way?

July 11, 2025
Fix Your Personal Finances Before Investing in Real Estate
When my students ask me a question about how to start investing in real estate, I tend to respond with a question of my own:

“How much savings does your personal budget generate each month?”

Yes, I know. It’s so annoying to answer a question with a question.

This particular question usually leads to a double dose of annoyance from my students.

My students are first annoyed that I ignored their question about real estate. They didn’t come to me to talk about something boring, like budgeting. They want to know about the exciting stuff, like becoming a real estate investor.

What I’ve noticed is that after this initial annoyance fades away, another form of annoyance sets in. My students get annoyed because they can’t actually answer the question.

They realize they have no idea how much money they’re saving each month because they don’t have a personal budget.

That’s a problem.

Not having a personal budget is a problem for anyone who wants to be a successful real estate investor.

Investing in real estate means running a business. Money comes in and money goes out. To be successful, you have to make sure that more money comes in than goes out.

This is obvious stuff, right?

The same logic applies to your personal budget: if you want to get ahead in life, more money needs to come in than goes out.

The problem is most people have a hard enough time managing their personal finances. How are they going to handle managing business finances?

That’s why I ask my students, “If you haven’t mastered this idea with your personal budget, are you sure you want to take on the stress and risk of an investment property?”

It would be much easier to simply invest in an index fund, like VTSAX. At least in that case, you don’t have to manage a business budget. You just have to do your best to constantly add money to your investment account.

It’s usually around this point when my students start nodding in understanding.

Before investing in real estate, make sure your personal finances are in order.

My goal here is not to dissuade you from investing in real estate. I am a big proponent of rental property investing.

I’ve said it before: I think every professional or lawyer can benefit from owning rental properties.

My only goal is to help you avoid the mistakes that crush so many beginner real estate investors. One of the biggest mistakes I see is people taking on a major financial commitment (and time commitment) without starting from a strong foundation.

If you’ve been following along on the blog, you likely noticed the progression in topics we’ve covered.

You’ll see links to each one of these topics featured on the top of the Think and Talk Money homepage:
- Money Mindset
- Budgeting
- Debt
- Credit
- Investing
- Real Estate
We initially covered each of those topics in order from top to bottom. First, we talked extensively about the mental side of money. Without having your money mindset in the right place, nothing else matters.

We then spent a lot of time talking about personal finance fundamentals, like budgeting, saving, and handling credit and debt responsibly.

Only after having our personal finance foundation in place did we talk about more fun concepts like investing and real estate.

There’s a reason we’ve covered these topics in this order.

If your money mindset is not in the right place, you won’t be able to stay on budget.

If you can’t stay on budget, you’ll likely fall into debt.

When you’re falling deeper and deeper into debt, it doesn’t make a lot of sense to prioritize investing.

Photo by Towfiqu barbhuiya on Unsplash

Why bother with real estate if any profits are just going to disappear?

Let’s focus on that last point for a minute.

What sense does it make to invest if you’ve never proven to yourself that you can use those investment gains responsibly?

I never want to see people take on the challenge of investing in real estate just to have any profits disappear because they don’t have a strong personal finance foundation in place.

Imagine someone does the work to find and sustain a good rental property that generates $1,000 per month in cash flow.

It’s not easy to earn that much. It takes time and effort, not to mention the risk involved.

If that same person blows the $1,000 he earned on things he doesn’t care about, what was the point?

Why take on the risk and do the work if the money will all be gone by the end of the month?

Unfortunately, this is how many people go through life. They work hard, make good money, and then have nothing to show for it.

I don’t want that to be your fate. I want you to have a plan for your money before you earn it.

That means sticking to a budget that consistently moves you closer to living freely on your terms.

Most of us don’t know where our next dollar is going.

The reason most people never get ahead with their finances is because they don’t have a plan for where their next dollar is going.

Their income hits their checking account, they spend it on this or that, and pretty soon that money has disappeared. They haven’t used the money to advance any of their priorities. It’s just gone.

To me, this is one of the most important money mistakes that we need to fix right away. We definitely need to fix it before we take a chance on investing in real estate.

If not, you’ll just be making the same mistakes, just with more money to lose.

Having a plan for our money, before we earn it, is essential if we want to reach our goals. With a plan, we can eliminate the disappearing dollars with confidence that our money is being used to serve our purposes.

How do you create a plan for your money before you earn it?

You need to have a budget.

If you don’t currently have a budget that results in excess money at the end of each month, I encourage you to start there before thinking bout real estate.

How to create a Budget After Thinking.

The key to budgeting is to eliminate disappearing dollars by creating a plan for Now Money, Life Money, and Later Money.

Your Later Money is what you’ll eventually use to accelerate your journey to financial freedom by investing in stocks or buying real estate.

1. Now Money

Now Money is what you need to pay for basic life expenses.

These expenses include housing, transportation, groceries, utilities (like internet and electricity), household goods (like toilet paper), and insurance.

These are expenses that you can’t avoid and should be relatively fixed each month.

2. Life Money

Life Money is what you are going to spend every month on things and experiences in life that you love.

This bucket includes dining out, concerts, vacations, subscriptions, gifts, and anything else that brings you joy.

We can’t be afraid to spend this money. This bucket is usually what makes life fun and exciting. The key is to think and talk so you are spending this money consistently on things that matter to you.

3. Later Money

Later Money is what you are saving, investing, or using to pay off debt.

This bucket includes long term goals, such as retirement plan contributions (like a 401k or Roth IRA), college savings for your kids (like a 529 plan), emergency savings and paying off student loan or credit card debt.

This bucket also includes any shorter term goals, like saving for a wedding or a downpayment for a house.

Most fun of all, this bucket includes any investments you make to more quickly grow your wealth, like investing in real estate or the stock market.

Later Money is the key category that fuels your ultimate life goals, like financial independence. The more you fuel this category, the faster you can reach your goals.

Photo by Kelly Sikkema on Unsplash

When you have strong fundamentals in place, money becomes fun.

Being good with money doesn’t have to be stressful. Once you have the fundamentals in place, you’ll start to see how each dollar you earn gets you one step closer to financial freedom.

Before you think about investing in real estate, make sure that your personal finances are in order.

Owning rental properties means running a business. When the money comes in, you want to make sure it doesn’t go right out.

Otherwise, the effort, stress, and risk of owning real estate is not worth it. Any dollar you earn is likely to disappear as quickly as it comes in.

To prevent that from happening, establish good money habits before you buy real estate.

In the end, you’ll be so happy that you did.

For any real estate investors out there, did you jump in before establishing strong personal money habits first?

What advice would you have for beginners thinking about investing in real estate?

Let us know in the comments below.
July 8, 2025
Use Common Sense to Help Identify Good Rental Properties
If you want to be a successful rental property investor, you need to buy good rental properties.

Good rental properties equal good tenants.

Good tenants equal less headaches.

Less headaches equal a longer holding period.

A longer holding period equals more cash flow, appreciation, debt pay-down, and tax benefits.

Add it all up and that equals more financial freedom.

And, it all starts with buying the right property.

How do I know if I’m buying the right property?

One of the biggest mistakes that beginners make is buying bad rental properties. The reality is that most properties that hit the market are not good rental properties.

I typically look at hundreds of properties online before finding any that are even worth walking through. Of the ones I walk through, less than 10% are worth buying.

Don’t waste your time by running the numbers on every property that hits the market. The numbers only tell part of the story, anyways.

Instead, the first step is to develop and commit to specific criteria for attractive properties in your market.

If a property does not meet your criteria, move on.

This will save you precious time, especially important if you are still working a full-time job.

It will also save you from the disappointment of visiting properties that looked good on paper but failed to meet your other requirements.

So, how do you develop a set of standards for quality rental properties in your market?

Use common sense and your own life experiences to develop criteria for your market.

Obviously, every market is different. Don’t believe anyone who tells you they have a one-size-fits-all solution for evaluating properties. What works in Chicago won’t necessarily work in Los Angeles.

However, regardless of what market you’re in, you can and should use common sense and your own life experiences to evaluate rental properties.

Don’t overcomplicate this part.

Before you do anything else, think about what you would personally want in a rental property.

Forget about complex formulas and deal metrics. We’ll get to the numbers soon enough.

Start with a basic question:

What would I want if I were a renter in this market?

Before anything else, write down a list of the most important features that you would want in an apartment. Then, use that list as a guide to finding the right kind of properties.

By the way, using your own common sense is one of the best parts about investing in real estate. You don’t need an advanced degree or a background in real estate.

We all have some idea of what makes a neighborhood a good place to live. The same goes for what makes an apartment a good apartment.

We may not always agree on what those things are, and that’s OK. It may be for a simple reason, like we are not targeting the same potential tenant pool.

The bottom line is you should absolutely use your common sense and life experiences to help formulate your investing strategy.

Ask yourself what you would want in an apartment. Don’t waste your time running the numbers on any property that doesn’t match your criteria.

I prefer to invest in properties that make sense to me.

Warren Buffett has famously said that he does not invest in companies or products that he doesn’t understand.

We can apply that same logic to rental properties. Invest in properties that inherently make sense to you.

If you are a buy-and-hold investor like I am, you are going to be dealing with a certain tenant pool in your market for years to come. You want to make sure that you understand that tenant pool so you can buy properties that will be appealing to them.

You also want to be able to effectively communicate with prospective applicants and current tenants. The best way to ensure that happens is by investing in markets that you understand.

Photo by Sawyer Bengtson on Unsplash

Work with a real estate broker and don’t be afraid to ask for help.

If you’re having trouble identifying the key factors to look out for in your market, ask around.

Talk to your colleagues and friends about what people in your target demographic look for in an apartment. Most of us tend to want the same things.

Of course, don’t underestimate the importance of working with a good real estate broker.

A good real estate broker can help you come up with a list of the most desirable features for renters in your market.

My wife and I have worked with the same broker for almost a decade now. He’s been a mentor to us and helped us come up with our list of key factors. More on that below.

He also knows exactly what we want in a property and doesn’t waste our time with properties that don’t match our criteria.

Having a good broker on your team is essential if you want to be a successful investor.

How I’ve used my life experiences to target rental properties in Chicago.

I invest in a Chicago neighborhood that typically attracts young professionals in their 20s and early 30s.

Why do I target young professionals in Chicago?

Well, I am one.

OK, fine.

I used to be one. Oof.

As a young professional in Chicago, I rented apartments throughout the city for nearly 15 years. Based on my own experiences, I have a good idea of what that demographic is looking for in an apartment.

I believe that gives me an advantage in targeting the right kinds of properties.

Plus, I teach nearly 100 law students each year and work with young professionals at my law firm. It’s a demographic that I’m comfortable with and still have a good understanding of what matters in a rental apartment.

Besides my personal experiences, why else do I target young professionals?

Generally speaking, young professionals earn consistent paychecks, are respectful to apartments, and are too busy to complain about minor issues.

All good things, as far as I’m concerned.

Location, location, location.

We’ve all heard the number one rule in real estate:

Location, location, location.

While a number of factors combine to make particular locations attractive, I’ll highlight one factor that’s very important to me in the Chicago market.

First, for a bit of context.

As mentioned earlier, I target properties in Chicago that would be attractive to young professionals.

Traditionally in Chicago, young professionals commute to office buildings in The Loop (Chicago’s downtown, central business district) via public transportation.

Yes, even in the “work from home” era, most young professionals living in Chicago commute downtown at least a couple days each week.

Since I know my ideal tenant likely commutes downtown, I look for properties that make commuting easier.

That means targeting properties near public transportation.

More specifically, I target properties within a half mile of the L (Chicago’s train system, short for “elevated.”)

Photo by Pablo Merchán Montes on Unsplash

I target properties close to public transportation because of my own experiences as a renter and because of what I’ve learned from potential tenants.

When I was renting apartments in Chicago, I always wanted to be close to the L. There’s nothing worse than walking 20 minutes to a train when it’s 10 degrees or 90 degrees outside.

It makes sense that now as an investor, I should target these same types of apartments close to public transportation.

Having done hundreds of apartment showings over the years, I’m confident that young professionals want to live close to public transportation.

I believe that the most desirable properties for young professionals are the ones close enough to an L station that people can walk there in 10 minutes or less.

Plus, coffee shops, restaurants, shops and other attractive offerings tend to be located near L stations.

So, in terms of location, proximity to the L is one of the most important factors for me.

No matter how attractive a property looks online, I’m not interested if it doesn’t satisfy this requirement.

What are some of my other top requirements for a rental property?

What I look for in a rental property may be different from what you look for. Use your own life experiences and common sense to decide if these elements would be beneficial in your market.

My wife and I have relied on our own life experiences, coupled with advice from our real estate broker, to come up with this list.

It’s not an exhaustive list, but here are some of the most important factors we evaluate when considering rental properties in Chicago:
1. Location, location, location. See above. Proximity to the L and social life (coffee shops, restaurants, bars, etc.) are crucial. Most of the young professionals we rent to are still in the “going out” phase of life. They want to live in fun neighborhoods so they can enjoy themselves when they’re not working. They typically stay in our apartments for 2-3 years, oftentimes before buying a place of their own and “settling down.”
2. Taxes. Property taxes can eat away your cash flow. We have high property taxes in Chicago across the board, but taxes vary widely from neighborhood to neighborhood. I look for properties in areas that have more attractive taxes.
3. Big bedrooms. One of the most common questions I get when I do apartment showings is, “Can I fit a king size bed in here?” People love big beds these days. This can be a challenge considering Chicago’s standard 25-foot wide lot. I look for properties with a minimum bedroom size of 10 x 10.
4. Outdoor space. Young professionals want to have outdoor space, even if they never use it. When I was a renter, I always wanted an apartment with a balcony for my grill. It didn’t matter to me that I only used it a handful of times each year. Maybe having outdoor space made me feel more grown up?
5. Parking. Even though Chicago is a very public transit-friendly city, people still like having cars. Because most young professionals aren’t using their cars every day, they want to keep it safe in a dedicated parking space.
There are certainly other factors we consider, but these are some of the first things I’m looking for when I look through listings on the internet.

These factors were important to me when I was a renter and are still important to the young professionals I rent to today.

While I don’t invest in other cities besides Chicago, I imagine these factors would also be important for young professionals everywhere.

What is your specific criteria for rental properties?

The fist step in purchasing good rental properties is having a set of specific criteria that match your needs and market.

Don’t overcomplicate it. Use your common sense and life experiences as a framework.

Run your criteria by your real estate broker and other investors in your market.

Only after you have come up with a list of important features should you worry about running the numbers.

Whether you currently own rental properties or are hoping to get started, what factors are most important in your market?

Let us know in the comments below.
July 6, 2025
Why do You Really Want to Own Rental Properties?

Before you start doing something, figure out why you’re doing it.

Someone smart probably said that at some point, right?

We’ve spent a lot of time recently talking about the main reasons why I invest in rental properties. We’ve also talked about the work involved with owning rental properties.

I’m a big believer in the power of real estate. I’ve also come to appreciate just how much work is involved in owning rental properties.

The reason I’ve spent so much time writing about the benefits and the work involved is to make sure you know exactly what you’re getting yourself into.

Once you fully understand and appreciate the benefits and the work involved, you’re ready for the next step:

Think and talk about why you want to own rental properties.

Depending on why you want to own rental properties, your strategy may be different than mine or someone else’s strategy.

The key is to figure out your “Why” before making costly mistakes, in terms of both money and time, that don’t help advance your goals.

Don’t skip this crucial step and jump right to analyzing deals.

The last thing you want to do is take on such a big commitment without truly knowing why you’re doing it.

To help you start thinking about a strategy, let’s review the benefits and also the work involved in owning rental properties.

You can read much more in my series on real estate here.

1. Rental property cash flow is king.

With cash flow, you can cover your immediate life expenses. For anybody hoping to reach financial freedom, it is essential to have income to pay for your present day life expenses.

For my money, cash flow from rental properties is the best way to pay for those immediate expenses.

If your present day expenses are already covered, you can use your cash flow to fund additional investments.

That might mean buying another rental property or investing in another asset class, like stocks.

2. Long-term wealth through appreciation.

Appreciation simply refers to the gradual increase in a property’s value over time.

While cash flow can provide for my immediate expenses, appreciation is all about the long-term benefits.

Like investing in stocks over the long run, real estate tends to go up in value. The key is to hold a property long enough to benefit from that appreciation.

To benefit from appreciation, all I really need to do is make my monthly mortgage payments, keep my property in decent condition, and let the market do the rest.

Photo by Brandon Griggs on Unsplash

3. With rental properties, other people pay off my debt.

When I buy a rental property, I take out a mortgage and agree to pay the bank each month until that mortgage is paid off. At all times, I remain responsible for paying back that debt.

However, I do not pay that debt back with my own money.

Instead, I rent out the property to tenants. I do my best to provide my tenants with a nice place to live in exchange for monthly rent payments.

I then use those rent payments to pay back the loan.

As my loan balance shrinks, my equity in the property increases. Equity is just another way of saying ownership interest.

When my equity in a property increases, my net worth increases.

4. Real estate investors earn massive taxes benefits.

When you earn rental income, you must report this income on your tax return. Rental income is treated the same as ordinary income.

However, the major difference between rental income and W-2 income is that there are a number of completely legal ways to deduct certain expenses from your rental income.

Common rental property expenses may include mortgage interest, property tax, operating expenses, depreciation, and repairs. We’ll touch on a few of these deductions below.

With all of these available deductions, the end result is that most savvy real estate investors pay little, or nothing, in taxes on their rental income each year.

Yes, you read that right.

I’ll say it again, just to be clear:

Most savvy real estate investors legally pay nothing in taxes on their rental income each year.

Do not own rental properties if you want passive income.

Now that you know the benefits, let’s highlight just how much work is involved in owning rental properties.

At one point or another, you may have heard someone say, “I want to invest in rental properties for some passive income.”

Yes, we all want passive income.

No, investing in rental properties is not passive.

Think of owning rental properties as a way to earn “semi-passive” or “partially-passive” or “somewhat-passive” income.

Don’t think of owning rental properties as a way to earn “passive” income.

If you want passive income, you should be investing in index funds, like VTSAX. For more on investing in the stock market, you can check out my series on investing here.

For me, the benefits of owning rental properties significantly outweigh the downsides of being a landlord. It’s a tradeoff that I would happily make again and again.

How does the old saying go? “If it were easy, everybody would do it.”

Being a landlord is not easy. It’s definitely not for everyone.

But, then again, neither is financial freedom.

In the end, if you are willing to put in the effort, owning rental properties will accelerate your journey to financial freedom.

Do you still want to own rental properties after knowing the benefits and the work involved?

Now, you know the main benefits and the work involved with owning rental properties.

Like I said, owning rental properties is not for everyone. It takes time and effort to learn the basics.

Then, it takes more time and effort to do your research and develop a strategy.

At some point, you’ll need to take a chance and make a purchase. That means putting your hard-earned dollars at risk.

None of this will be easy.

But, it sure is a lot of fun.

And, there is a lot of upside.

If you still want in, I’m going to help you get started.

Photo by Aaron Sousa on Unsplash

Ask yourself: what are my main goals in owning rental properties?

Before you start analyzing deals, you need to think long and hard about what your goals are.

Depending on what your’e trying to accomplish, your strategy is going to be different.

For example, are you looking to move to an expensive neighborhood and just want to offset your ownership costs?

You may benefit from owning a home with a coach house, granny flat, or garden unit. You can then live in the primary unit and rent out the second unit to reduce your monthly costs.

Or, your goals might be to leave full-time employment and use rental property cash flow to fund your life. In that case, you’ll need a property that generates significant cash flow, possibly at the expense of personal comfort or long-term gains.

On the other hand, you may love your job and have no plans of leaving anytime soon. You’re not concerned about present day cash-flow. Instead, you’re looking for long-term gains through appreciation, debt pay-down, and tax benefits.

In this scenario, you may target markets that have shown strong growth but don’t necessarily cash flow.

These are just a few possible considerations. One of the things I love most about investing in real estate is how many options there are. It’s up to you to decide what options are most attractive for your goals.

This is why the first step is to think and talk about why you want to own rental properties.

Don’t ignore this first step. Spend some serious time thinking about what you’re trying to accomplish.

Because different properties may offer different benefits, you need to commit to a strategy before you start worrying about how to analyze specific deals.

Too many beginner investors skip this step and realize much too late that a property they bought doesn’t help achieve their goals.

My goal in owning rental properties is to accelerate my journey to financial freedom.

My wife and I invest in rental properties in Chicago and Colorado to accelerate our journey to financial freedom.

In order to be truly financially free, we need cash flow to cover our present day expenses. So, we’ve targeted properties in Chicago that generate strong monthly cash flow.

Don’t get me wrong, we certainly hope to benefit from appreciation, debt pay-down and tax advantages. That’s why we’ve chosen to invest in neighborhoods that we think are only getting better.

However, we view those long-term gains as more of a bonus. Our focus with our Chicago properties is on present day cash flow.

On the other hand, our Colorado property is a long-term play. It does not generate positive cash flow. That said, we use the rental income to help offset our ownership costs.

We are planning to keep our Colorado condo in our family for decades to come. Offsetting the ownership costs with rental income will help us accomplish that goal.

At the same time, we are hoping that our Colorado condo appreciates in value, making it a solid long-term investment. So, even though it does not generate cash flow for us, it still fits into our long-term plans for financial freedom.

One key point: just because my wife and I invest for cash flow doesn’t mean we are planning on leaving full-time employment.

I am a big proponent of all lawyers and professionals having multiple streams of income. I refer to these various income streams as Parachute Money.

Because my wife and I are earning steady paychecks, we’ve been able to use our cash flow for other investments. We have multiple income streams and are putting all those income streams to work. That’s one reason we’ve been able to scale our portfolio so quickly.

What are your goals in owning rental property?

You now know the benefits, the work involved, and some different strategies to consider regarding rental properties.

Now, it’s time to ask yourself why you want to own rental properties.

Once you figure out the “why,” you can then move onto the “how.”

So, if you’re considering owning rental properties, what is your why?

What goals are you trying to accomplish?

Let us know in the comments below.

July 3, 2025
Do Not Invest in Real Estate if You Want Passive Income
Turbo 200 Universal Capacitor 67.5MFD: $501.00

Add Puron-410A, Replace Valve, Freon Charging: $729.00

CO2 Drain Purge, Remove Water: $437.00

2 Ton R 410A Coil: $2,000.00

Total for A/C Repairs: $3,667.00

If you’re thinking that’s a rough year for air conditioner repairs, you wouldn’t be wrong.

Unfortunately, those are all repairs we’ve needed on different units in the past 10 days.

It gets better (worse?)… the average high temperature in Chicago over the past ten days has been around 90 degrees.

Still want to own rental properties?

Why would anyone want to own rental properties?

We’ve spent a lot of time recently talking about the four main reasons why I invest in rental properties:
When these benefits combine, real estate investors can generate significant wealth over the long run.

But, make no mistake:

Owning rental properties does not generate passive income. Being a landlord is a job. Even if you rely on a property manager, it’s still a job.

Before we talk about the job of owning rental properties, here’s a quick breakdown of each of the four main benefits.

For a more detailed description of each benefit, you can read my series on investing in real estate here.

1. Rental property cash flow is king.

With cash flow, you can cover your immediate life expenses. For anybody hoping to reach financial freedom, it is essential to have income to pay for your present day life expenses.

For my money, cash flow from rental properties is the best way to pay for those immediate expenses.

If your present day expenses are already covered, you can use your cash flow to fund additional investments.

That might mean buying another rental property or investing in another asset class, like stocks.

2. Long-term wealth through appreciation.

Appreciation simply refers to the gradual increase in a property’s value over time.

While cash flow can provide for my immediate expenses, appreciation is all about the long-term benefits.

Like investing in stocks over the long run, real estate tends to go up in value. The key is to hold a property long enough to benefit from that appreciation.

To benefit from appreciation, all I really need to do is make my monthly mortgage payments, keep my property in decent condition, and let the market do the rest.

3. With rental properties, other people pay off my debt.

When I buy a rental property, I take out a mortgage and agree to pay the bank each month until that mortgage is paid off. At all times, I remain responsible for paying back that debt.

However, I do not pay that debt back with my own money.

Instead, I rent out the property to tenants. I do my best to provide my tenants with a nice place to live in exchange for monthly rent payments.

I then use those rent payments to pay back the loan.

As my loan balance shrinks, my equity in the property increases. Equity is just another way of saying ownership interest.

When my equity in a property increases, my net worth increases.

4. Real estate investors earn massive taxes benefits.

When you earn rental income, you must report this income on your tax return. Rental income is treated the same as ordinary income.

However, the major difference between rental income and W-2 income is that there are a number of completely legal ways to deduct certain expenses from your rental income.

Common rental property expenses may include mortgage interest, property tax, operating expenses, depreciation, and repairs. We’ll touch on a few of these deductions below.

With all of these available deductions, the end result is that most savvy real estate investors pay little, or nothing, in taxes on their rental income each year.

Yes, you read that right.

I’ll say it again, just to be clear:

Most savvy real estate investors legally pay nothing in taxes on their rental income each year.

Photo by Bernie Almanzar on Unsplash

Rental properties do not generate passive income.

At one point or another, you may have heard someone say, “I want to invest in rental properties for some passive income.”

Yes, we all want passive income.

No, investing in rental properties is not passive.

Think of owning rental properties as a way to earn “semi-passive” or “partially-passive” or “somewhat-passive” income.

Don’t think of owning rental properties as a way to earn “passive” income.

If you want passive income, you should be investing in index funds, like VTSAX. For more on investing in the stock market, you can check out my series on investing here.

For even more, JL Collins literally wrote the book on investing in VTSAX. His book is called The Simple Path to Wealth and is tremendous. You can read my review here.

By the way, there’s nothing wrong with wanting passive income. For those of us on our journeys to financial freedom, passive income is what it’s all about.

It’s just that owning rental properties is not passive.

To be a successful rental property investor, you have to appreciate that it is a job.

Owning rental properties is like having another job.

It’s not a full-time job. In fact, there might be months that go by when you don’t actually do much of anything. Your main job is to be at-the-ready in case a tenant messages with an issue.

On the other hand, there will be 10-day stretches where you have three a/c units break requiring multiple service calls, tenant coordination, and $3,600 in repairs.

Granted, this 10-day stretch was just about the worst stretch for maintenance and repairs we’ve had as landlords. It just so happened to occur in the days leading up to me writing this post about being a landlord. Life’s funny, huh?

Still, talk to any landlord and they will have similar stories to share about the stress involved with being a landlord.

Photo by Jon Tyson on Unsplash

Most rental property investors who give up did not realize the work involved.

I’ve known countless rental property investors over the years.

In my experience, the ones who end up selling their rental properties after a couple of years did not appreciate that becoming a landlord means taking on a job.

Unfortunately, they sell their properties long before getting the benefits from cash flow, appreciation, debt pay-down, and tax advantages.

These landlords had likely been misled into thinking that owning rental properties was an easy way to generate passive income.

Look back at the top of the post for the four main reasons I invest in rental properties.

Cash flow, appreciation, debt pay-down, and tax benefits.

Did I say anything about easily earning passive income?

Don’t make the same mistake that so many unsuccessful landlords have learned.

If you’re considering your first rental property, don’t fool yourself into thinking you’ll be earning passive income. There will be tenant issues, work orders, money spent, and tough decisions to be made like in any other business.

This remains true even if you have a property manager. You’ll often hear real estate investors griping about “managing the property manager.”

The bottom line is owning rental properties is a job. It’s not a full-time job. It’s not even a regular part-time job. But, it is a job.

At times, it can be very easy. Other times, it’s very stressful.

If you can handle the job, you can generate massive long-term wealth for you and your family.

I accept that owning rental properties is a job and have benefitted immensely.

For me, the benefits of owning rental properties significantly outweigh the downsides of being a landlord. It’s a tradeoff that I would happily make again and again.

How does the old saying go? “If it were easy, everybody would do it.”

Being a landlord is not easy. It’s definitely not for everyone.

But, then again, neither is financial freedom.

Coming up, we’ll talk about tips on how to make your experience as a landlord as smooth as possible. You can also follow me on socials for current issues I’m dealing with as a landlord.

In the end, if you are willing to put in the effort, owning rental properties will accelerate your journey to financial freedom.

Are you a rental property investor?

Do you agree that owning rental properties is a job?

Let us know in the comments below.
July 1, 2025
Invest in Real Estate for Massive Tax Benefits

When was the last time you took a look at your actual pay statement?

Most of us working W-2 jobs have direct deposit, meaning our paychecks are automatically deposited into our bank accounts. On pay day, all we have to do is wake up, open our banking app, and confirm we got paid.

When we do this, all we see is our net pay, or take-home pay. Our net pay is what we earn after all deductions are subtracted from our gross pay.

Deductions may include voluntary contributions, like to our 401(k) and HSA, as well as other benefits, like health insurance.

That’s all nice so far.

Not so nice is that our paychecks are further reduced by mandatory tax withholdings.

For high earning lawyers and professionals, taxes can easily reduce our W-2 income by 25%-40%.

This is not groundbreaking news to anyone, right?

As employees, we are accustomed to having significant taxes withheld from our paychecks.

We’ve become so accustomed to paying taxes as W-2 employees that none of this should surprise us. Taxes are just part of the bargain when you’re an employee.

Well, what if I told you that automatically paying taxes every month does not have to be part of the bargain?

In fact, I know of a way to make money where taxes can be reduced or deferred for a long time, if not eliminated altogether.

And, that means you get to keep and benefit from more of your hard-earned money each month.

This leads us to the fourth main reason I invest in real estate:

Real estate offers massive tax benefits.

I earn income through W-2 employment and rental properties.

As a W-2 employee and a real estate investor, I know firsthand that not all income is created equal.

My W-2 income is heavily taxed every month.

My rental property income is not.

Today, we’ll introduce some of the main reasons why real estate investors pay less in taxes than W-2 employees.

Before we talk about these tax benefits, let’s review the first three reasons why I invest in real estate. Each of these reasons has accelerated my journey to financial freedom.

Note: I am not an accountant or tax professional, so please be sure to consult with an expert for tax advice for your personal situation.

1. Rental property cash flow is king.

With cash flow, you can cover your immediate life expenses. For anybody hoping to reach financial freedom, it is essential to have income to pay for your present day life expenses.

For my money, cash flow from rental properties is the best way to pay for those immediate expenses.

If your present day expenses are already covered, you can use your cash flow to fund additional investments.

That might mean buying another rental property or investing in another asset class, like stocks.

2. Long-term wealth through appreciation.

Appreciation simply refers to the gradual increase in a property’s value over time.

While cash flow can provide for my immediate expenses, appreciation is all about the long-term benefits.

Photo by Jason Briscoe on Unsplash

Like investing in stocks over the long run, real estate tends to go up in value. The key is to hold a property long enough to benefit from that appreciation.

To benefit from appreciation, all I really need to do is make my monthly mortgage payments, keep my property in decent condition, and let the market do the rest.

Now that we’ve reviewed how cash flow and appreciation work together to generate long-term wealth, we can look at the additional benefits of debt pay-down.

3. With rental properties, other people pay off my debt.

When I buy a rental property, I take out a mortgage and agree to pay the bank each month until that mortgage is paid off. At all times, I remain responsible for paying back that debt.

However, I do not pay that debt back with my own money.

Instead, I rent out the property to tenants. I do my best to provide my tenants with a nice place to live in exchange for monthly rent payments.

I then use those rent payments to pay back the loan.

As my loan balance shrinks, my equity in the property increases. Equity is just another way of saying ownership interest.

When my equity in a property increases, my net worth increases.

On top of monthly cash flow, appreciation, and debt pay-down, the tax benefits offered to real estate investors is another way to generate wealth through real estate over the long run.

Let’s take a look at some of these massive tax benefits.

What are the primary tax benefits to investing in real estate?

When you earn rental income, you must report this income on your tax return. Rental income is treated the same as ordinary income.

However, the major difference between rental income and W-2 income is that there are a number of completely legal ways to deduct certain expenses from your rental income.

Photo by The New York Public Library on Unsplash

Common rental property expenses may include mortgage interest, property tax, operating expenses, depreciation, and repairs. We’ll touch on a few of these deductions below.

With all of these available deductions, the end result is that most savvy real estate investors pay little, or nothing, in taxes on their rental income each year.

Yes, you read that right.

I’ll say it again, just to be clear:

Most savvy real estate investors legally pay nothing in taxes on their rental income each year.

Would you rather have rental income or W-2 income?

This post is not meant to be a primer on income taxes, but we can use a very basic tax bracket calculator to highlight the distinction between rental income and W-2 income.

I currently receive both types of income so readily appreciate the difference in how each form of income is taxed.

Let’s say you live in Illinois and are a high-earning lawyer or professional making a gross annual income of $250,000. Based on 2024’s federal tax rates, you will owe $53,015 in federal income tax. That’s 21% of your income.

Source: taxact.com

Illinois is one of the 42 states that also levies a state income tax. Illinois levies a flat state income tax of 4.95%. For our example, that means an additional $12,375 in taxes each year.

In total, a W-2 employee earning $250,000 in Illinois pays $65,390, or nearly 26%, in income taxes each year.

Again, this is not meant to be a tax primer. And yes, most W-2 employees take the standard deduction, meaning they’ll get a small refund when they file their tax returns.

Still, there’s no getting around the reality that when you’re a W-2 employee, you have limited options to reduce your taxable income.

In the end, you will pay a significant percentage of your income to the government every year.

On the other hand, real estate investors have a number of legal tax deductions at their deposal.

That means a real estate investor earning $250,000 in rental income likely pays very little, or even nothing, in income taxes.

How is that possible?

Let’s find out.

How is it that real estate investors pay so little in income taxes?

The federal government has long encouraged investment in real estate. People need places to live, work, and socialize. The government long ago decided to reward investors who take on the risk of providing these opportunities.

The key way the government incentivizes real estate investors is through tax deductions.

To accomplish its goal, the government allows real estate investors to deduct certain rental property expenses from their income.

Photo by Sonnie Hiles on Unsplash

As mentioned above, common rental property expenses may include mortgage interest, property tax, operating expenses, depreciation, and repairs.

When properly tracked and reported on your tax return, these expenses can oftentimes negate all the rental income you earned.

For today’s purposes, I’ll highlight one key deduction that shows just how much the government wants to encourage real estate investment:

Depreciation.

What is Depreciation?

Depreciation is an accounting method that allows real estate investors to deduct some of the cost of owning a property over time.

This accounting process is not a trick and is completely legal.

Calculating your property’s depreciation can get complicated and is best left to the tax professionals.

In general terms, if you own residential rental property and use standard depreciation like me, you can deduct the cost of owning that property over 27.5 years.

Each year, you can then reduce your rental income by that annual depreciation.

Here’s an example to help illustrate how depreciation works.

Let’s say you buy a rental property for $500,000, and the closing costs are $10,000. The property’s in excellent shape so no capital improvements are needed.

That means your total initial cost for this rental property is $510,000.

When you buy a rental property, you are actually buying the land and the building. Your city, county or town’s assessor typically attaches a value to each the land and the building.

For depreciation purposes, only the value of the building is depreciable. The land is not.

In our example, let’s say the land was valued at $110,000. You are not allowed to depreciate the value of the land.

So, your depreciable basis is the initial cost of the property less the land value:

Initial Cost – Land Value = Depreciable Basis

$510,000-$110,000=$400,000

For residential rental properties, you can spread out that depreciable basis over 27.5 years to figure out the annual depreciation.

Depreciable Basis / 27.5 = Annual Depreciation

$400,000 / 27.5 =$14,545.45

What this means is that you can deduct $14,545.45 from your rental income each year.

Combined with the other available deductions, you can see why real estate investors end up paying very little, or nothing at all, in rental income taxes each year.

Note: If you sell your rental property, you are responsible for paying depreciation recapture tax, which is a topic for another day. To keep it simple, depreciation recapture is a non-factor for this conversation for many reasons. The most important reason for that is because you have to pay this tax even if you never claimed depreciation on your tax return.

Your tax professional will help ensure you get all the tax benefits for owning rental properties.

Fully understanding taxes is not easy. That’s why we have licensed professionals to help us.

A concept like depreciation can be very complicated. Rest assured that your tax professional will help you benefit as a real estate investor from all the available tax breaks.

The point of today’s post is to introduce you to the definitive truth that the tax code favors real estate investors.

While we barely scratched the service today, hopefully you can start to see why it is so advantageous from a tax perspective to own rental properties.

Photo by Kelly Sikkema on Unsplash

I personally earn rental income and W-2 income.

When you legally deduct your rental property expenses, it’s likely that your taxable rental income for the year will be reduced to nothing.

Compare this reality to that of a high-earning W-2 employee, who regularly pays between 25% and 40% in income taxes each year.

The W-2 employee needs to earn significantly more money to take home as much as the rental property investor.

I personally earn rental income and W-2 income.

One source of income hits my bank account in full on the first of every month. I never worry about taxes.

The other source of income gets drastically reduced by taxes before I ever see a dime.

Which type of income do you think I prefer earning?

How about you?

June 27, 2025