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Real Estate Development and Urban Renewal: Lessons from the Field

Written by Evan Ross | Apr 8, 2026 12:00:00 PM

Welcome back to another episode recap from the Real Estate Tax Playbook! I'm Evan Ross, your host, and I had the pleasure of sitting down with Bill Chapman, a seasoned real estate developer based out of Richmond, Virginia, who has been transforming the Roanoke market for close to 20 years.

From Sports Radio to Real Estate Development 

Bill's journey into real estate development is anything but traditional. After graduating from VCU with a journalism degree in the early 1990s, he was working in sports radio for the Richmond Times Dispatch and the University of Virginia Sports Network while bartending to supplement his income. It was through his work at a popular downtown Richmond restaurant that he met the entrepreneurial elite who were just beginning to rehabilitate downtown Richmond. 

"I was living downtown in one of maybe two or three rehabilitations that had been completed," Bill shared. "I was living in an old warehouse, thought it was the coolest thing in the world. And so was kind of on the ground level of sort of seeing it happen." 

This ground-floor perspective led to an opportunity in project management, where Bill managed 18 projects within a five-year period during Richmond's downtown transformation. 

The Roanoke Discovery 

Bill's introduction to Roanoke came through Granger McFarland, a state senator whose son was a Richmond-based developer. Despite initial reluctance due to his busy schedule, Bill decided to take a day trip to explore Roanoke's potential. 

"I remember coming downtown and seeing that there was already this sort of critical mass of restaurants and entertainment, which is really important for multifamily and why people live downtown," Bill recalled. When he saw Salem Avenue for the first time - an area locals described as where "all the prostitutes hung out 20 years ago" - Bill recognized the potential in what he called "the best concentration of high quality warehouses." 

His instincts proved correct. Within six to seven months, when three buildings became available, Bill drove down, saw them, and put them all under contract before they even hit the market. 

Building the West Station District 

Over the years, Bill has been instrumental in creating what's now known as the West Station District in Roanoke. His projects include: 

Fulton Motor Lofts (2008) 

This 22-unit condominium project was Bill's first Roanoke venture. Remarkably, they sold all but two units before the 2008 financial crash, thanks to Roanoke's delayed economic cycle compared to larger markets. 

The Lofts at West Station 

A two-phase project totaling 142 apartments, which also brought Beamer's 25 (the neighborhood's first restaurant) and later Big Lick Brewing Company to the area. 

Parkway 301 

An 89-unit project in the former Shenandoah building, where the Blue Ridge Parkway was designed on the sixth floor and managed for over 30 years. 

416 Micro Farms 

A smaller seven-apartment building that introduced Tuco's taqueria, which Bill credits with establishing the neighborhood as "the cutting edge neighborhood for new concepts." 

A Developer's Nightmare: The Parkway 301 Crisis 

Not every project goes smoothly, and Bill shared one of his most challenging experiences at Parkway 301 in March 2013. During demolition, they discovered that the building's transfer beams - critical structural elements added when the building was expanded from three to seven stories - were completely rusted out. 

"Our engineer comes on site, looks at it says, I have no idea how this building is even standing right now. You need to get everyone out of the building immediately," Bill recounted. 

The situation required bridge shoring companies rather than typical building shoring, and there were only two such companies available - one in Washington, DC, and one in North Carolina's Triangle area. With limited competition, they essentially set their own prices. 

To make matters worse, just a week after this discovery, the historic tax credit investment market collapsed due to a court case in New Jersey involving a questionable partnership structure. Bill's investor, Sherwin Williams, pulled out, leaving him with a massive structural problem and no financing partner. 

"There was not a lot of sleep in March of 2013," Bill admitted. 

Despite these setbacks, Bill persevered, eventually finding a new investor (though a difficult one) and completing the project. The experience taught him valuable lessons about due diligence and resilience. 

Current and Future Projects 

Bill is currently working on his most challenging project yet: 501 Salem Avenue, the former Sunlight Bakery building that's been vacant for 30 years. The building presents numerous structural challenges, but Bill sees it as essential for expanding the West Station District across Fifth Street. 

"We're kind of at the stage in Roanoke where most of the best buildings have been taken at this point," he explained. "This is by far the biggest eyesore. It gives us an opportunity to expand over Fifth Street, which sort of starts the next wave of development moving further west." 

The 33-apartment project is expected to be completed by the end of summer 2025. 

The Rewards and Challenges of Historic Rehabilitation 

After 25 years in historic rehabilitation, Bill finds the work incredibly rewarding despite its challenges. "You never get used to the before and the after," he said. "To know that you are helping to improve a community and to save its most cherished assets is greatly rewarding." 

However, he notes growing challenges in the review process, particularly the disparity between state and federal government interpretations of the same regulations. Despite these hurdles, Bill remains committed to the work because "it's too important." 

Key Takeaways for Developers 

Based on our conversation, here are some key insights for aspiring or experienced developers: 

  1. Due Diligence is Critical: Bill's structural crisis at Parkway 301 could have been avoided with more thorough initial investigation, particularly in complex, multi-story buildings. 
  1. Market Timing Matters: Sometimes it's skill, sometimes it's luck. Being aware of market cycles and having flexibility can make the difference between success and failure. 
  1. Relationships Are Everything: From Bill's introduction to development through restaurant connections to finding tenants through referrals, relationships drive the business. 
  1. Resilience is Required: Major setbacks are inevitable in development. The ability to adapt and persevere through challenges like structural problems or market collapses is essential. 
  1. Community Impact Drives Success: Bill's focus on improving neighborhoods and preserving historic assets has created lasting value beyond individual projects. 

Looking Ahead 

The Roanoke market continues to show strong demand for downtown housing, with no signs of slowing down. While challenges exist - particularly in affordable housing financing - developers like Bill continue to see opportunities for community improvement through thoughtful rehabilitation of historic properties. 

For those interested in learning more about Bill's work or connecting with him, you can visit his website at BillChapmanInc.com or reach out directly at bill@billchapmaninc.com. 

As always, thank you for following along with the Real Estate Tax Playbook. If you're interested in the technical aspects of historic tax credits, I recommend pairing this episode with Pat Murtaugh's previous episode on the tax implications of historic rehabilitation projects. 

Listen to the complete conversation below, including Bill's insights on youth baseball training technology and more detailed project discussions.