Flipping to Midterm Rentals: Ashton Hines on Investment Strategies for the DFW Market

Written by:

Steve Marcinuk

Date:

21 Jun 2025

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“I’ve always appreciated real estate because I can walk up to a property and touch the front pillar—it’s tangible. I understand there are only a few variables affecting value, whereas the stock market or more complex investments like syndications are areas I don’t comprehend as thoroughly,” says Ashton Hines, real estate agent with Keller Williams Dallas Preston Road and co-host of The Real Estate Heavyweights podcast.

Hines brings a unique perspective to the Dallas-Fort Worth market as both an agent serving traditional buyers and an active investor with multiple flips and rental property investments under his belt. His journey from theory to practice offers valuable insights for anyone considering the DFW market.

From Rich Dad, Poor Dad to Real-World Experience

Like many investors, Hines traces his interest in real estate to Robert Kiyosaki’s seminal book. “My journey started in my junior year in college. I was stuck at my friend’s apartment for hours without a car, and he had Rich Dad, Poor Dad there,” Hines recalls.

That initial exposure planted the seed, but it would be nearly 15 years before Hines took concrete action. After obtaining his license about five years ago, his first two flips went smoothly. It was his third project, a much larger renovation, where he encountered significant challenges.

“When I got in trouble with my third flip, I reached out to a friend of a friend who worked in real estate in Dallas,” Hines explains. That connection was with Tavis Westbrook, an experienced investor who had completed over 200 flips. Their collaboration not only helped Hines navigate his challenging project but eventually led to the creation of their podcast, Real Estate Heavyweights.

“We were essentially recording the conversations we were having at the flip, discussing what to do, what to avoid, what to be careful about, and talking about the market in general,” says Hines of the podcast’s origins.

The Midterm Rental Opportunity

While the DFW market has attracted significant attention from out-of-state investors, Hines has found that many struggle with managing renovation projects remotely.

“Many out-of-state investors assumed it would be straightforward, find off-market properties, assemble a crew, and flip. That proved quite challenging,” Hines notes. “I discovered the importance of regularly visiting the job site, which is nearly impossible for distant investors.”

Instead, Hines has identified a more viable strategy: midterm rentals. These properties, which typically rent for periods of 1-6 months, occupy a sweet spot between traditional long-term rentals and management-intensive short-term vacation rentals.

“I’ve placed several investors in midterm rentals because they’re more forgiving,” Hines explains. One successful example involved properties near hospitals that cater to traveling nurses on 14-week assignments. “Those traveling nurses receive housing allowances. If you have a conveniently located condo available at a reasonable rate, you can withstand occasional vacancies.”

Hines has identified an even more lucrative niche within this space: insurance placements. “When someone’s house suffers fire or flood damage, they need temporary housing for several months, whatever their insurance policy covers. These typically command premium rates.”

These insurance-backed rentals can be particularly profitable for higher-end properties. “If you own a million-dollar home, insurance should place you in something comparable. They can’t simply relocate you to a house 30 minutes from your child’s school just because it’s inexpensive.”

While this strategy requires more upfront capital, Hines believes it offers a compelling alternative to the highly competitive lower-end market. “Everyone wants that $200,000 off-market house they can invest $50,000 in and make a quick profit. Finding these opportunities is extremely difficult due to intense competition.”

Key Lessons from 100+ Podcast Episodes

After more than 100 episodes of The Real Estate Heavyweights, Hines has distilled several crucial lessons:

1. Master renovation sequencing: “Where do you start? When do you bring in the next contractor? How do you manage overlapping work? That was my major mistake in my third flip. I scheduled carpet installation before completing demolition, then had to bring back the sheetrock crew. Proper sequencing makes everything significantly smoother.”
2. Take action: “I read Rich Dad, Poor Dad in college, nurtured the dream, and consumed content for years. Eventually, you must take concrete steps. Once you do, you can speak from actual experience rather than theory.”
3. Match investment strategy to personal goals and strengths: “Define your goal. Is it monthly cash flow? An equity play? What’s your competitive advantage? What’s your risk tolerance?”

Navigating Current DFW Market Conditions

As of June 2025, the Dallas market is experiencing unusually high inventory levels. “Some statistics indicate a 10-year high,” Hines explains. “However you analyze it—months of inventory, days on market—we’re having to adjust expectations downward.”

This reality has forced Hines and Westbrook to modify their approach. “We’re being more conservative with projections and increasing estimated renovation costs, up to $5 per square foot more than usual, to account for unexpected issues and extended holding periods.”

Despite these challenges, Hines remains optimistic, citing predictions about interest rates. “If rates drop into the fives by year-end and absorb some inventory, the fall may behave more like a typical spring market. Warren Buffett anticipates that fall will actually be the busy season this year due to declining interest rates.”

The partners are maintaining their ambitious goals despite the challenging market. “We aim to complete 20 flips this year. We’re currently on pace for about 15, but we’ve had some very successful projects where we purchased well and executed effectively.”

Succeeding in Any Market

Regardless of conditions, Hines emphasizes the importance of discipline and understanding your investment parameters. “You can succeed in any market. You just need to be extremely disciplined about what makes a project viable for you.”

For their flipping business, this means maintaining high standards. “We have established quality standards we’re comfortable with. We’re willing to walk away from properties we can’t purchase at the right price. Our priority is delivering finished homes that genuinely excite buyers.”

This approach continues to yield results even in a challenging market. “At an open house yesterday for Tavis’ latest flip, we received multiple offers within 24 hours. It will sell well above asking price due to strategic pricing and quality finishes.”

Hines also shares a warning from a local attorney who represents hard money lenders: “They’re experiencing numerous property repossessions and foreclosure proceedings. Hard money loans are difficult to sustain right now, many deals lack sufficient margin to service that financing long-term.”