From Fix & Flips to Section 8 Landlord: How Dillon Eversole Built 6 Figure Profits in Affordable Housing

Why This Episode Matters

On the Affordable Housing & Real Estate Investing Podcast, host Kent Fai He welcomes Dillon Eversole, a real estate investor who turned early struggles as a young agent into a profitable career in affordable housing. Dillon’s story is especially powerful for investors, developers, and housing advocates because it shows how fix-and-flip profits can be strategically rolled into long-term Section 8 rentals that deliver stable cash flow and community impact.

How Did Dillon Eversole Get Started in Affordable Housing?

Dillon began as a 19-year-old real estate agent with little success. Cold calling friends in college dorms wasn’t working, but he soon discovered a niche: helping investors buy distressed properties. Acting almost like a wholesaler, he created value by finding overlooked deals. Eventually, he transitioned into flipping single-family homes, and those profits became the seed money for his Section 8 rental portfolio.

“I started with flips, but realized the income stopped the moment I didn’t have another deal. Rentals gave me stability and impact.” – Dillon Eversole

What Markets Does Dillon Invest In and Why?

Dillon began flipping in Tampa, Florida, but quickly realized that cash flow potential was stronger in the Midwest. He turned to HUD’s Fair Market Rent (FMR) data, calculating rent-to-price ratios to target the best markets.

• In St. Louis, Missouri, he found properties that rented at 1.4% to 1.5% of purchase price.
  
  

• In Cleveland, Ohio, he achieved closer to 2%, often earning $2,000 a month on duplexes purchased for around $100K.
  
  

By comparing FMR to purchase prices, Dillon identified high-demand Section 8 markets with long waitlists, ensuring steady tenant placement.

How Do You Evaluate Section 8 Deals Like Dillon?

Dillon shared a simple formula anyone can use:

1. Go to HUD’s FMR database and look up average rents.
   
   

2. Multiply by 12 to annualize.
   
   

3. Divide by the average purchase price in the area.
   
   

If the ratio is above 1% (ideally 1.5–2%), the market is worth considering. This approach allows investors to “snipe” the best cash flow markets instead of wasting time analyzing random deals.

What Are Dillon’s Best and Worst Deals?

Best Deal:

• Bought a Tampa property for $75,000 that sat on the MLS for almost a year.
  
  

• It had foundation damage, delinquent tenants, and was in a rough neighborhood.
  
  

• After negotiating foundation repairs down from $90K to $15K, he fixed it, rented it for $2,250/month, and later sold it for $265,000, netting six figures.
  
  

Worst Deal:

• His very first flip went sideways after hiring the wrong contractor.
  
  

• Paid $25K with little work done, then had to spend another $45K to finish.
  
  

• The lesson: don’t cut corners on contractors, and always get multiple quotes.
  
  

What Lessons Did Dillon Learn About Section 8 Inspections?

Section 8 can be a landlord’s best friend—guaranteed rent, huge waitlists—but inspections can be frustrating. Dillon stressed:

• Expect subjective calls (like missing caulking or an upside-down outlet).
  
  

• Mentally budget $1,000 per unit for inspection fixes.
  
  

• Play by the rules, even if you disagree, to avoid costly fines and delays.
  
  

“If you play the Section 8 game, you need to play by the rules. Fighting inspectors costs more than just fixing the issue.” – Dillon Eversole

Key Insights for Affordable Housing Investors

• Roll profits forward: Use flips to fund long-term rentals.
  
  

• Target cash flow ratios: Aim for 1.5–2% rent-to-price markets.
  
  

• Account for repairs: A roof costs the same in Cleveland as Tampa—budget accordingly.
  
  

• Leverage home warranties and insurance: They protect against $1K–$2.5K repair “dead zones.”
  
  

• Respect tenants: Good Section 8 tenants deserve landlord support. Treating them well creates long-term stability.
  
  

Best Quotes from Dillon

• “I didn’t want flipping to be my only source of income. Rentals gave me sustainability.”
  
  

• “A roof is still a roof. Whether in Tampa or Cleveland, it costs the same, so plan for it.”
  
  

• “Some of the best deals come with the hardest lessons.”
  
  

• “Taking care of people always comes back to you tenfold.”
  
  

Common Questions About Section 8 Investing

Q: How do I find the best markets for Section 8 rentals?
A: Use HUD’s FMR database, compare rents to average purchase prices, and target markets with strong ratios (1.5–2%).

Q: Is Section 8 reliable for rent payments?
A: Yes. Public housing authorities pay on time, and most markets have long waitlists, meaning no extended vacancies.

Q: How much should I budget for repairs?
A: Dillon sets aside about 30–35% of rents for maintenance and capital reserves, much higher than the 8–10% often cited in other podcasts.

Q: Are Section 8 inspections hard to pass?
A: They can be nitpicky, but the key is to mentally budget for fixes and work with inspectors rather than fighting them.

Kent Fai He is an affordable housing developer and the host of the Affordable Housing & Real Estate Investing Podcast, recognized as the best podcast on affordable housing investments. His mission is to provide everyday investors with the tools, knowledge, and connections to build wealth while solving America’s housing crisis. Episodes like this highlight practical strategies and real-world lessons investors need to succeed.

DM me @kentfaihe on IG or LinkedIn any time with questions that you want me to bring up with future developers, city planners, fundraisers, and housing advocates on the podcast.