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Investor Stories: From Self Managing Properties to Living in the Florida Keys

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Let’s face it. If you’re anything like most landlords –your properties are their life. They’re your biggest investment, savings, and security for the future. Often, they represent years of sacrifice and hard work.

So when it comes to overseeing those properties, naturally, it’s easy to feel that the best person for the job is yourself!

But the truth is, while owning income property can be tremendously rewarding –it can also be stressful, and incredibility time-consuming as well. After a while, being a DIY landlord can start to feel a lot less appealing, and a lot more time-consuming than what you first signed up for. Pretty soon many landlords find that all of those phone calls and maintenance requests can start to take their toll. Especially if you own multiple rentals or properties that are out of town –or, even if you’d like to take a vacation someday.

This is exactly the situation that real estate investors JD and Michelle Dickerson found themselves in. While their properties represented their future –they required a tremendous time commitment, something that compounded with every property they invested in.

The Dickersons had started investing in Houston in 1992 and had amassed a total of 26 properties. Managing them alone was a herculean task; something that was a constant source of stress and frustration to JD –and his family.

As a self-manager, there were plenty of 2:00 am phone calls.

“It seems like the A/C would always go out at one in the morning,” says JD.

JD and Michelle were stretched thin, and there wasn’t much time for the family. They often talked and dreamed about taking a family vacation to the Florida Keys, but as the years went by, that dream began to look increasingly distant. Stress mounted as the Dickersons struggled to find a way to make some much-needed time-off a reality. One day, the Dickerson’s oldest son came to JD and asked him why he was stressing out about a trip…that wasn’t ever going to happen.

“You know you’re not going to do it, you’re not going to leave your houses,” he said.

That was a turning point for JD, and he realized that it was time to make some changes.

He needed more freedom; and wanted to be able to spend time with his wife and kids, to be there for them.

After searching for a solution, JD realized that outsourcing his tasks to a property manager was the way to go.

He soon landed upon Renters Warehouse –and realized almost immediately that this was the answer that he’d been looking for.

“They’re not just talking the talk, they’re walking the walk as well,” says JD.

For many people the thought of giving up control of their properties can be difficult –but the Dickersons found that Renters Warehouse’s property management services gave them freedom.

Property Managers Make Life Easier

Property managers mean less stress and more freedom –here’s a look at how that breaks down practically.

There are a number of practical benefits that come from hiring a property manager:


  • Reduce Tenant Turnover

A good property manager can help you to reduce tenant turnover. They’ll be able to provide a quick turnaround time for maintenance and repairs requests, and will also have a network of reputable professionals that they can turn to for fast and quality work.

  • Help You Fill Vacancies

Going through an experienced property manager can help to fill those vacancies fast. A good property manager will know how to write ads, take great photos, and where to advertise your rental. They’ll also be skilled at setting competitive prices for the area, and ideally, will offer thorough tenant screening that can help your property to get rented –quickly, and most importantly, to qualified tenants.

  • Keep You in Compliance With the Law

Finally, a good property manager will be familiar with local, state, and federal law –and will be able to oversee your property in a way that’s in compliance. This means that paperwork –including tenant applications and rental agreements will be written in a way that’s in-line with the law –and processes like security deposit collection and return, lease enforcement, evictions, and more will all be handled the right way as well. This is especially crucial if you own properties in different states, and need to keep track of different legislation.

As for the Dickerson family, JD said that the money he pays out for property management has been absolutely worth it.

“Being in charge of our time is priceless,” says JD. “My stress level is way down. My blood pressure is way down. Just more relaxed. I’m not getting that call at 2:00 am that, ‘my toilet’s stopped up.’”

“I get all the rent money, and they handle all the problems.”

Renters Warehouse freed up JD Dickerson and his family to visit the Florida Keys. But their story doesn’t end there. Thanks to the fact that they were able to outsource the entire property management process, JD and his family decided to extend their Florida stay –indefinitely.

They’re still in the Keys to this day, and are living every day on their own terms –paddle boarding, boating, and fishing –spending time together as a family.

“Renters Warehouse is freedom,” says JD. It’s really about our lifestyle.

“We live on an island in the Florida Keys,” he continues. “And it’s a dream come true for us.”

“It’s such a more relaxed atmosphere that we have more downtime with the kids,” adds Michelle. “We spend a lot of time just going out on the boat. We look for wildlife and nature. We’ll come back and jump in the pool.”

“We’ve learned to appreciate the sunsets,” says JD. “And it’s all because of Rent Estate.”

Want to see more stories like this one? Check out The Matt McKinney Story: From Construction to Owning Rental Properties.

What would financial freedom look like to you? If you’d like help creating an investing strategy, reach out to a Renters Warehouse’s Rent Estate™ Advisor and see how you can make your goals of financial freedom a reality.


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