Tag: Real Estate Team

Be Sure to Have an Experienced Accountant on your RE Team
I invest in real estate for the massive tax benefits.

In fact, the massive tax benefits are one of the four main reasons why I invest in real estate. The other three reasons are cash flow, appreciation, and debt pay-down.

I’ve previously written about how I earn rental income and legally pay close to nothing in income tax on my rentals each year.

How is that possible? Am I some type of tax wizard?

Of course not.

But, I do have a tax wizard on my real estate team.

OK, more accurately, I have a Certified Public Accountant (CPA) on my real estate team.

Your accountant is so integral to your financial success that he is the next person you need to have on your real estate team.

Why is it so important to have an accountant on your team?

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.

These incentives come largely in the form of tax benefits.

The challenge for real estate investors is to actually take advantage of all these tax incentives.

That’s where your accountant comes in.

Because I work with an accountant, I don’t have to be a tax expert. I just have to know enough to have intelligent conversations and make decisions when the time comes.

My accountant makes sure I get all the tax benefits for owning rental properties.

Before talking further about accountants, let’s review the first three members that you’ll want to have on your real estate team.

Your Spouse is the Most Important Person on Your RE Team

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

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?

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

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.

Build Out Your RE Team Starting with a Five-Star Broker

Once you and your spouse are on the same page, it’s time to start building out the rest of your real estate team.

Start building your real estate team by finding a great broker. Your broker is like a five-star hotel concierge who can make your entire experience so much better.

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

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

The best brokers are in it for the long run and will help you navigate challenges as they pop up. 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.

Photo by Medienstürmer on Unsplash

How to Evaluate a Great Mortgage Broker for your RE Team

With a five-star real estate broker on your team, it’s time to find a great mortgage broker.

A great mortgage broker is like a tour guide who is the local expert and knows the ins-and-outs of the neighborhood. She has an intimate knowledge of the local food scene based on years of experience.

She’ll show you the hidden gems and recommend what to order at each restaurant based on your personal preferences. She can educate you as to what’s in certain dishes and why you may like to try them.

She’ll also steer you away from the tourist traps and prevent you from going to the wrong places to ensure you have the best experience possible.

Recommendations? Education? Preventing mistakes?

Love all those things.

And, this is exactly what a good mortgage broker will do for you.

A good mortgage broker will:
- Recommend the best loan for your goals.
- Stop you from borrowing more than you really can afford.
- Help get your loan approved.
- Explain the numbers.
- Not let you refinance until the time is right.
Take your time finding a good mortgage broker. It’s important to work with someone who does more than just promise the best rates and terms.

With your spouse, a five-star real estate broker, and a great mortgage broker on your team, it’s now time to fill out the rest of the key positions.

Seek out an accountant with real estate specific experience.

I mentioned earlier that 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.

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.

The key is to work with someone who has significant experience specific to rental property investing.

The truth is there are numerous tactics and strategies that apply to real estate investors that don’t apply to all businesses.

An accountant who may be ideal for a restaurant owner or law firm might not be a good fit for real estate investors.

This is not a knock on accountants, either. In this day and age, professionals in all industries tend to specialize in niche areas.

For example, I am a lawyer who specializes in helping people with mesothelioma. You wouldn’t hire me to represent you in a divorce.

If you broke your foot, you wouldn’t go see a brain surgeon.

You get the idea.

When seeking out an accountant, be sure to work with one who has experience specific to real estate investing.

How can you tell if an accountant has experience specific to real estate investing?

When my wife and I were searching for an accountant, it became very clear to us that not all accountants work with real estate investors.

For instance, most accountants are well-versed in common rental property expenses. These common expenses may include mortgage interest, property tax, operating expenses, depreciation, and repairs.

We met with plenty of intelligent accountants who understood these basics.

Photo by Scott Graham on Unsplash

But, we wanted more than just basic help. We wanted help in crafting a long-term strategy for achieving financial freedom through real estate.

When you start meeting with accountants, ask them how many real estate investors they work with. Ideally, you’ll find an accountant who works with a number of investors similar to you.

You’ll also want to find an accountant whose style matches yours. Some accountants are more aggressive and some accountants are more conservative.

For example, say you own a vacation condo that you rent out sometimes and use personally other times. You may get different advice from two accountants on what counts as a rental property deduction for that condo.

It’s ultimately up to you to find an accountant that matches your style.

Find an accountant who answers your phone calls.

Maybe this goes without saying, but you want an accountant who answers the phone when you call. As investors, we never know when an opportunity may pop up that we need timely advice on.

You might be surprised how many real estate investors don’t have an open line of communication with their accountants. I think it’s a mistake to only consult your accountant after you’ve gone ahead with a decision.

As one example, a few years ago, I thought about buying an 8-unit apartment building with a number of partners. It seemed like a good way to earn some cash flow with only a small amount of my own money in the deal.

Before I moved ahead with the deal, I called my accountant. We had a long chat about all the additional complexities involved from a tax perspective.

He took the time to educate me so I could make a good decision. In the end, I walked away from the deal.

If I didn’t have a good relationship with my accountant, I might have made a big mistake.

A good accountant will help you reap the massive tax benefits of investing in real estate.

As a real estate investor, you don’t have to be an expert in every part of the business.

There’s no better example than when it comes to taxes.

Find a good accountant who is willing to educate you and strategize with you. You want more than just someone to prepare your tax returns.

When you have a good accountant on your real estate team, you’ll move that much faster towards financial freedom.

What other traits should real estate investors look for in a good accountant?

Let us know below.
July 20, 2025
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