December 31, 2025
#165 Building a Smart STR Portfolio: Lessons from Parker Borofsky
Building a successful vacation rental business often feels like a balancing act between cold, hard data and that quiet voice in your gut that says, “This is the one.” When you are looking to grow, the most valuable perspective you can find is someone who has seen the industry from both sides of the closing table. That is why I sat down with Parker Borofsky, a premier lending expert who made the jump from financing thousands of deals to building her own impressive portfolio. Our conversation was a masterclass in building a smart STR portfolio by combining high-level strategy with grounded intuition.
The Lender’s Edge: Seeing Under the Hood
Parker’s journey into investing began while she was serving as the lender for Avery Carl. While she was helping others secure their first rentals, she was also getting an “under the hood” look at what truly makes a property successful. As a lender, she saw the bank statements and the actual Airbnb deposits flowing into her clients’ accounts.
She realized that if she knew the mortgage payment and could see the revenue, she had the perfect blueprint to start her own journey. This unique vantage point allowed her to begin building a smart STR portfolio starting in 2018, eventually expanding from the Smoky Mountains into the Florida Panhandle and Kentucky.
Balancing the Numbers with Your Intuition
One of the most powerful lessons Parker shares is that your gut instinct is often a better guide than you give it credit for. She recalls purchasing a massive five-bedroom lodge in Townsend, Tennessee, right before the world shut down in 2020. While many investors were strictly looking at the most popular markets, Parker saw the value in seven hundred feet of river frontage and a unique “swinging bridge”.
Even though the “numbers” were uncertain because the area wasn’t a primary tourism hub yet, her intuition told her the uniqueness of the property would win out. Today, those Tennessee cabins are the most profitable properties in her entire portfolio. Building a smart STR portfolio requires you to be brave enough to look where others aren’t looking.
Stewarding a Legacy: The Frank Lloyd Wright House
Serendipity played a major role in Parker’s latest acquisition: the only Frank Lloyd Wright-designed home in Kentucky, known as the Ziegler House. Named after a place she visited at age twenty, Parker even named her daughter Taliesin after Wright’s famous studio. When the house popped up on her feed, she didn’t just see an investment; she saw a piece of history to steward.
Building a smart STR portfolio isn’t just about collecting keys; it’s about creating an experience. Parker and her husband are thoughtfully weaving the property’s 1910 history—including its connection to Marion Mahoney, one of history’s first prominent female architects—into the guest experience. By focusing on the story, she turns a simple stay into a bucket-list destination.
For more resources on architectural preservation and the legacy of Frank Lloyd Wright, you can visit the Frank Lloyd Wright Foundation.
Navigating the Challenges of Unique Appraisals
When you invest in one-of-a-kind properties, you will inevitably face challenges with traditional financing. Appraisers rely on recently sold, similar homes, but how do you find a “comp” for a Frank Lloyd Wright masterpiece? Parker had to do her own research, looking at prominent historical homes as far as thirty miles away to provide the appraisal department with the necessary data.
She emphasizes the importance of collaboration between your agent, your lender, and yourself. By being prepared for a lower appraisal and having the data to support her case, she was able to navigate the underwriting process and secure the deal.
Modern Lending Strategies for Real Estate Investors
If you are looking to grow your property portfolio in 2026, Parker suggests exploring trending mortgage products that offer more flexibility than a standard conventional loan.
- Bank Statement Loans: Ideal for self-employed borrowers with complex income. Lenders look at deposits over twelve months rather than net tax returns.
- DSCR Loans: These focus on the property’s income potential. Parker recommends sticking to a one-year prepayment penalty to maintain your flexibility.
- 1099 Loans: Perfect for real estate agents, using 1099 income without requiring full tax returns.
The secret to building a smart STR portfolio is being prepared for the house that finds you. Start by connecting with an experienced loan officer now, so when your “Frank Lloyd Wright moment” happens, you are ready to boss up and take the leap.
Click here now to listen to the full podcast.
HIGHLIGHTS AND KEY POINTS:
[01:00] A short introduction about our guest Parker Borofsky, and how she got into investing in short-term rentals
[03:00] Parker walks through her growing short-term rental portfolio across Tennessee, Florida, and Kentucky, highlighting a pivotal purchase in Townsend, Tennessee
[08:43] Parker explains how intuition, timing, and storytelling led her to an unexpected Kentucky purchase
[13:01] Parker shares how stewardship and storytelling shape the experience of owning a Frank Lloyd Wright home
[18:56] Parker reflects on the emotional full circle of stewarding a historic Frank Lloyd Wright home
[21:24] Parker dives into the complexities of securing a mortgage for a one-of-a-kind Frank Lloyd Wright home, emphasizing that unique properties often create appraisal challenges
[26:51] How to handle appraisal challenges for unusual properties, emphasizing preparation, collaboration, and clear communication
[31:24] Parker talks about the mortgage options that are trending for real estate investors, particularly for self-employed borrowers or those with complex income streams
[34:57] The importance of connecting with experienced loan officers as a critical first step for anyone looking to grow their property portfolio in 2026
[37:13] Genuine appreciation for Parker’s commitment to giving back to the short-term rental industry, and Parker’s role as a speaker at the upcoming Short-Term Rental Virtual Summit for Women
[38:30] The lightning round
Golden Nuggets:
- “It’s not always perfect when you’re finding properties in the market. So, go and see and feel and trust your gut feeling.”
- “It’s so important that we balance the numbers with our intuition.”
- “Look ahead of what’s coming.”
Let’s Connect!
Website: wealthbuildersmortgage.com
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