How Gabriel Silva and Yvan Rojas Are Redefining Affordable Housing Development in Boston

Why This Conversation Matters

Affordable housing is one of the toughest challenges facing cities today, and the developers willing to take it on are often misunderstood. In this episode of the Affordable Housing & Real Estate Investing Podcast, host Kent Fai He sits down with Gabriel Silva and Yvan Rojas, two Boston-area developers navigating zoning battles, community resistance, and the realities of building projects with affordable set-asides.

Their stories are a blueprint for anyone who wants to step into development, scale past single-family investing, or better understand the role of Section 8 tenants in real estate. More importantly, this conversation highlights how affordable housing is about more than numbers — it’s about humanity, community, and vision.

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.

How Do First-Time Developers Break Into Multi-Million Dollar Deals?

Most investors start small — a single-family rental, a duplex flip, or maybe a BRRRR strategy. Gabriel Silva took a different route. His very first real estate transaction was nearly $1 million: a piece of land approved for a 20-unit, five-story building with three affordable housing set-asides.

Instead of waiting until he “felt ready,” Gabriel reverse engineered the deal, studied zoning laws, attended city planning meetings, and learned directly from what other developers were getting approved or denied. By setting his personal standard at no projects under 16 units, he pushed himself into scale from day one.

Lesson: Start with scale in mind. Even if you don’t land your first big project, preparing for larger deals forces you to understand zoning, financing, and long-term exit strategies.

What Are Affordable Housing Set-Asides and Why Do They Matter?

One of the biggest insights from this episode was how affordable housing set-asides work. In Boston and nearby cities, developments above a certain unit threshold must dedicate a percentage of homes to affordability.

For Gabriel’s 20-unit building, that meant three affordable units, allocated through a lottery system. These requirements are a balancing act: they give working families access to new housing, but they can also compress developer margins.

As Gabriel explained, without cooperation from cities or incentives like tax credits, the math can discourage builders from taking on these projects. That’s why advocacy and transparency are essential — so communities understand that developers are often absorbing real costs to deliver housing the city desperately needs.

Are Section 8 Tenants Really “Bad Renters”?

Yvan Rojas offered a powerful perspective on dispelling Section 8 myths. Early in his career, he managed a three-family in Brockton with all Section 8 tenants. Later, he inherited more voucher tenants when buying foreclosures at auction.

His experience? Section 8 tenants are no different than market tenants. Some are challenging, most are responsible, and almost all just want safe, clean housing for their families.

“Every Section 8 tenant I’ve come across has just been good people. They take care of their homes, they go to work, they raise their kids. It’s their space.” – Yvan Rojas

Kent and Yvan both emphasized that the stigma is outdated. The key to success with any tenant — Section 8 or otherwise — is clear communication and respect.

How Do Developers Handle Community Pushback?

One of the hardest realities for developers is NIMBY resistance. Gabriel shared how projects with affordable units often face neighbor opposition:

• Residents protest traffic, density, or changes to their neighborhood.
  
  

• Planning boards sometimes ask developers to shrink projects, which also shrinks the number of affordable units created.
  
  

• Community meetings can get hostile, even when the development adds needed housing stock.
  
  

Despite this, Gabriel pointed out that without the approval of earlier projects, like the tower where his own parents still live, many immigrant families — including his — would never have had access to housing in Boston.

This underscores the irony: today’s opposition often forgets that yesterday’s developments provided the very homes they live in.

What Role Do Mentors and Relationships Play in Real Estate Development?

Both Gabriel and Yvan stressed the importance of mentorship and networking. Yvan’s first exposure came from managing a friend’s Section 8 property. That relationship grew into introductions with foreclosure experts and seasoned developers.

Their advice is simple:

• Show up. Attend zoning meetings, community boards, and industry conferences.
  
  

• Add value. Even if it’s small tasks like sweeping an office, find a way to contribute.
  
  

• Be patient. Avoid rushing into deals without analysis, but don’t get stuck in paralysis either.
  
  

• Find mentors. Learning from those who’ve executed deals is the fastest way to grow.
  
  

As Yvan put it:

“It’s actually very easy to find a mentor if you dedicate yourself. Show up, work hard, and most experienced developers will be glad to teach you.”

Key Insights for Affordable Housing Investors

• Think bigger from the start. Setting a minimum deal size forces you to learn development at scale.
  
  

• Affordable set-asides are real. They create opportunity for families, but also require developers to navigate slim margins.
  
  

• Section 8 tenants deserve respect. The stigma doesn’t match reality — communication and empathy go a long way.
  
  

• Community pushback is part of the job. Developers must balance vision with patience and diplomacy.
  
  

• Mentorship accelerates growth. Relationships, not just capital, are the true foundation of real estate success.
  
  

Best Quotes from the Episode

“If you just let us build, you’d see how quickly we could solve the affordable housing problem.” – Gabriel Silva

“Every Section 8 tenant I’ve met has been a good person. They want to take care of their homes and families.” – Yvan Rojas

“Most people don’t believe they can do it, so they don’t go deep. But if you believe, you’ll show up to zoning meetings, talk to developers, and learn what it really takes.” – Gabriel Silva

Common Questions This Episode Answers

What are affordable housing set-asides?
Set-asides require developers of larger projects to dedicate a percentage of units to affordability, usually filled by lottery.

Are Section 8 tenants harder to manage?
Not necessarily. Like all renters, experiences vary, but communication and respect prevent most issues.

Why do neighbors fight affordable housing projects?
Often due to concerns about traffic, density, or change. Unfortunately, this resistance can reduce the number of affordable units delivered.

How do new developers protect themselves?
By planning multiple exit strategies, underwriting conservatively, and seeking mentorship before diving into big projects.

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 equip everyday investors, developers, and advocates with proven strategies that deliver both profit and impact.

DM me @kentfaiheon 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.