How to Rent Out Your House with Property Management in Florida

When you continue as a rental property investor or you rent out your house, which is the right time to hire a property management company in Florida, especially in 2025?

Is it after a certain number of units or after you have made a certain amount of money, or should you go ahead and hire a management company right from the start, which is the question that I am going to tackle in today’s edition, and we are just getting started?

Many of you have this question on your mind about when you should hire a property manager, or maybe you should hire one first, and I am going to give you some specific ideas on how you can decide in your own situation when you should do this or if you should do this.

There are different approaches that are both effective, and both can work as a real estate investor.

How to Know Your Need

My Situation

I’ll tell you about my situation first. When I started investing in real estate, I was 23. I had a business partner. We started flipping houses. But slowly but surely, we started getting some rental properties. We have a house in Florida and also had flats. We rented them out, and we managed those properties ourselves, not with property management companies at that time. So we collected the rent. We handled the maintenance calls. And that’s how we kind of built a system, understanding how to run our properties and explaining the rent process to the company. This is myself.

Learning the Business

And I think if you have the ability to do that, it’s always a good idea to learn the business from the ground up. I’m an old maxim business in that way: if you have a shop or a store, first learn to sweep the floor of the store, like learn to do the work of the world so you can be ready to do other things. And stop shooting and use that to stop. Every metaphor in a real estate investing book is property management. And so it can’t hurt if you really want to learn all the details about the business to do it a little bit yourself. And that’s what we did to get started.

Experience with Hiring a Property Manager

Hiring Our First Help

But we finally got to the point where we started hiring someone. We hired a bookkeeper just to help with a few things like checking mail and doing some things like that. But then she was really good at it, and she had better skills, and so we hired her to do more work. She started helping us with some of the collections on our rental properties. Eventually, she started signing up with the help of the application. At home at that point, we can do it all digitally.

But she became about 90 percent of our property management business that she would handle internally. I was still the person who signed the lease and did some things, but she took over a lot.

Traveling and Expanding Responsibilities

To the point where I traveled to Ecuador with my family in 2009 and 2017, and she could handle it a little bit. We managed it wherever I was. Originally, he decided to retire. Unfortunately, other things were going on, and so now we have outsourced everything to different property management companies. I would say 99% of it. My wife and I still manage a couple of our own properties. Then our business partner and I still have some of the odd situations where we either manage a third company that is either out of our area.

Managing Different Types of Rentals

Especially the ones that are a little bit more time consuming. We have college student rentals; they have a lot of turnover, and the leasing process takes a little bit longer. There are a few more maintenance calls with apartments than with single family houses. So our situation is we have outsourced almost all of it to property management companies.

My Mentor John Schaub

But let me tell you about another guy that I’ve seen as a mentor for a long time named john Schaub. He’s in Sarasota, Florida. He wrote a book called Building Wealth One House at a Time. He’s been in this business for over five decades, and he’s had, I believe, about 30 single family homes.

But I still don’t know the exact number of all those, where he knows about the number of them himself. He’s been through some other management processes, but he’s found that especially with single family houses, and he kind of has this privilege of what kind of single family houses he likes that attract a lot of self-sufficient tenants that stay for a long time.

They’re really easy to manage. Every time you need turnover and leases, and you know, there’s a punch list here and there, he can invest. But he can invest all the…

Lifestyle of a Smart Investor

That I’ve always seen who has the best lifestyle is really flexible. They’re training their kids in sports, traveling and their activities. So if you buy certain properties, especially small and powerful real estate investors, the kind of mindset that I advocate is to keep it as small or as large as possible so that you can buy your properties and you can fulfill your purpose.

Going Back to the Question

But let’s go back to the question. So there are two different examples of how you can do this, when you should do it. It’s multiple units. I think that’s a different standard than saying that you should hire a property manager after you get to a certain number of units.

That’s my own journey as a rental property investor to tell you those two different stories and also whether you have to manage different types of jobs. Show you different types of properties.

What John has done, or do you move to a different approach where you hire all your own property management services like I have done.

Achieving Flexibility and Balance

In both cases, you can achieve the same goal, which is to have flexibility for a lifestyle where you have a lot of time to do what you do. Where you have income coming in to pay for your lifestyle.

And then the other side of the coin, so that you also serve and look after those who enjoy your properties as much as your tenants. And take good care of your tenants.

The properties, so that it all works together. There are different ways to accomplish that. But the other point of this story, especially in my case, is that it can change over time. I think that was Melody’s original question, when you know you need to transition.

Learning and Starting Out

So let’s assume you’re listening to her. Either you start doing it yourself, as I suggested. You have a good way to learn your business. You may be learning the management company business. Or you are starting a brand new one, and you are not quite sure what to do from the beginning.

Why You SHOULD Hire a Property Manager

When to Hire a Property Manager

In both cases, I think there are three different situations where I would recommend not becoming a property manager yourself and hiring someone to do the work for you.

Not Interested in Becoming a Property Manager

The first situation is if you are not interested in becoming a property manager. It could be right away, like if you are just like, I don’t want to be a property manager. I am not interested in leasing properties. I have no interest in learning the business and just want to be an asset manager in that level of detail.

Managing from a Higher Level

That it is perfectly legitimate to manage you from a higher level, but there may be a legitimate reason for you. Do you know that business you were interested in learning? You wanted to do it for a period of time, but then you outgrew that interest. And like, you okay, I learned to do it, now I want to do something different.

Hiring Someone When Interests Change

Is it now permissible to hire someone when that happens? Is it on one property, or is it on five properties? But if you feel like no one is at a certain number, then you don’t have anyone.

Advice for Self-Management

Here is an important piece of advice from the beginning to start self-management. Even though you are paying to manage it yourself, you need to increase your numbers. When you buy a rental property, you are paying someone else to do it. Even if you manage it for the rest of your life, you need to build in management fees and whatever the cost is.

Financial Considerations

You know, I use 10% in my area. And if you are using those types of rates to manage my property, 10%, and build in that. If you manage it yourself, you pay yourself a lot of money. But if you lose interest, if something changes in your life, you are able to outsource financially.

Working for Free and Side Hustles

Think about this situation where someone made a deal with themselves by not paying themselves a management fee. They are basically working for free. You have justified the deal with that side hustle you have, because you have reduced the amount of money that you will have to do a little bit of work. And you need to do the work that will put themselves to work on something else and not pay themselves money for it.

Long-Term Benefits vs. Today’s Motivation

You are doing this as a real estate investor, and yes, it has long term benefits. Yes, I know all that, but today’s money is important. That motivates you. That will help you avoid losing interest.

Summary

So this is a related topic on a side cause. Make sure you need to pay a number. You’re not interested in being a property manager, whether it’s in the beginning or hiring someone else down the road to do it, which is perfectly fine.

Situation Two: Long Distance or Lack of Local Knowledge

Long Distance Property Management

Another situation where managing the property yourself probably doesn’t make sense is if you’re long distance. If you’re buying a property that you’re in California that’s in Miami, Florida, it’s going to be very difficult, if not impossible, to manage it yourself.

Hybrid Management Option

There are situations where you might have a hybrid where you hire a leasing agent to manage the property. And from there, you’re shown ten difficult tasks. You know, using technology and communication, you can do that kind of situation. But you still have someone on the ground helping you.

Having a Team Member on the Ground

So I think that’s a legitimate situation from the beginning, whether it’s your first property or your 10th property. Having a team member on the ground is a big advantage to you in the long distance. And it’s even more beneficial because you know the important things like the key steps to help you practically.

Expert Knowledge and Market Insight

Having someone on the ground who knows the market. When I’m buying properties, my first call to a third party is to my property manager to ask them what this property will rent for or what the trend is in this neighborhood. What you’re seeing here is that they are on the ground. They are the experts. And so you can lean into their knowledge, and that way, you are taking practical steps to put together practical technical steps for them.

Mentorship and Guidance

Another mentor is there to help you make you a better real estate investor.

Hiring a Management Company When Local Knowledge Lacks

And the other situation is long distance or not being in the real estate market. Even if you are close, but you don’t know the local market as well, this is a great reason to hire a management company. But remember, as I said in the previous situation, make sure you can build in your numbers so you can pay someone.

Situation Three: Need for Expertise or Extra Time

The third situation where it makes sense to go ahead and hire a property management company and rent out your house or flat as we rent out our Florida house in 2025 is when you have a real estate strategy or need some expertise or some extra time to invest in real estate.

The one I’m thinking about specifically is your Airbnb. My wife and I have a house that we rent out only for game days in Miami, Florida.

Conclusion

Rent out your house in Florida with property management is not just about how many properties you own in 2025—it’s about your goals, your time, and your lifestyle.Some people want to be hands-on landlords, while others prefer to focus only on growing their investments. The right time to bring in a property management company depends on your personal situation.

If you don’t want the headache of tenants, repairs, and calls at odd hours, then a property manager is the smart choice. If you live far away and can’t handle local issues quickly, they become even more valuable. And if you’re running short-term rentals like Airbnb or other high-turnover properties, then you need systems and expertise that a management company already has.

Yes, starting with self-management teaches you the basics, but as your life, business, and rental portfolio grow, doing everything yourself starts costing you time and energy. At that point, hiring a property manager isn’t just an expense—it’s an investment in stability, freedom, and long-term income.

A good property management company will keep your rentals profitable, reduce your stress, handle tenants professionally, and give you the freedom to enjoy life—whether that’s spending more time with family, traveling, or looking for your next big investment.

So, when should you hire one? The answer is clear: hire a property management company the moment it helps you earn more, stress less, and live the lifestyle you’re building your rental business for.