Closing Deals That Create Impact: Coliving Workforce Housing with Drew Oquendo

Why this episode matters for affordable housing investors

When it comes to affordable housing, deals don’t just appear out of thin air—you need someone who knows how to close. In this episode of the Affordable Housing & Real Estate Investing Podcast, host Kent Fai He sits down with Drew Oquendo, a Marine Corps veteran, investor, and master closer. Drew shares how he built his career from wholesaling and fix-and-flips to creating cash-flowing coliving rentals that provide workforce housing near major employers like Amazon.

For investors and advocates looking to scale, Drew reveals the mindset, skill sets, and tactical numbers behind converting single-family rentals into profitable affordable housing solutions.

What does it cost to convert a home into workforce coliving housing?

One of the most practical parts of Drew’s story is his transparency about costs. He breaks down how he turned a standard house into an eight-bedroom, three-bath coliving rental:

• Renovation quotes came in at around $9,000 for drywall, vents, and egress compliance.
  
  

• Furnishing ran $450–500 per room, including locks, digital keypads, and basic furniture.
  
  

• All-in, he spent about $25,000 on conversion plus furniture.
  
  

This setup positioned the property as a “mini-multifamily,” perfect for housing workforce tenants employed at nearby facilities.

How do you make money as a closer in affordable housing?

Drew doesn’t just close deals—he structures them to get paid upfront. He calls it “acquisition feasible”:

• Always raise slightly more capital than the base costs so you make money day one.
  
  

• On joint ventures, split acquisition fees so both partners win.
  
  

• Use management platforms like PadSplit to streamline operations and utilities.
  
  

The result: one property that was initially projected to lose $500 a month was restructured into a positive $1,600 monthly cash flow.

What skills make someone a true closer in real estate?

Drew’s Marine Corps discipline, combined with training under real estate coaches and the SubTo community, sharpened his skills:

• Discipline and repetition: Role-playing scripts daily, running calls, and refining closing skills.
  
  

• Authenticity: “Your vibe attracts your tribe.” Sellers and investors trust you when you’re genuine.
  
  

• Versatility: Closing isn’t just about sellers. It’s also raising capital, persuading buyers, and negotiating with lenders.
  
  

As Drew says, “A closer can close anybody—capital partners, sellers, or buyers. The skillset is universal.”

How does PadSplit and coliving create affordable housing opportunities?

Affordable housing doesn’t always require building new units. Drew explains how platforms like PadSplit make existing rentals accessible and profitable:

• Tenants pay weekly, often around $200 per room, making housing more affordable for hourly workers.
  
  

• Landlords earn strong gross rents by converting single-family homes into multiple coliving units.
  
  

• This strategy fills the gap where traditional market rents no longer match wages.
  
  

For investors, coliving offers a scalable entry point into affordable housing without waiting for government programs or LIHTC allocations.

Key Insights from Drew Oquendo

• Converting single-family homes into coliving rentals can turn negative cash flow into four-figure positive cash flow.
  
  

• Closing is not about scripts—it’s about authenticity, discipline, and reps.
  
  

• Affordable housing opportunities often lie in creative financing and specialized exit strategies like coliving or sober living.
  
  

• Your past experiences—whether in the military, sales, or another career—are assets that make you a unique closer.
  
  

Best Quotes from Drew Oquendo

“I always raise a little more to make money upfront. You want an acquisition feasible deal.”

“Your vibe attracts your tribe. If you’re authentic, the right sellers and partners will want to work with you.”

“A closer isn’t just closing sellers. A closer closes capital partners, buyers, and anyone needed to make the deal work.”

Common Questions This Episode Answers

How much does it cost to convert a rental into coliving housing?
Typically around $9,000 for basic renovations and $450–500 per room for furnishings.

Can you make money with affordable housing rentals near break-even cash flow?
Yes. By restructuring into coliving, Drew turned a projected loss into $1,600 positive monthly cash flow.

What makes someone a successful real estate closer?
Discipline, role-play practice, authenticity, and the ability to close with sellers, capital partners, and buyers.

What is PadSplit and how does it help affordable housing?
PadSplit is a coliving platform where tenants rent individual rooms by the week, making housing affordable while maximizing investor returns.

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.

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.