Building a successful vacation rental portfolio isn’t just about numbers—it’s about strategy, intuition, and having the confidence to trust both. In this episode, we explore what it really looks like to invest with intention, think long-term, and build a business rooted in education rather than hype.

In today’s episode, I sit down with the incredible Parker Borofsky, whose passion for lending and vacation rental investing shines through every story she shares. From her early days as Avery Carl’s lender to becoming a seasoned investor herself, Parker offers a behind-the-scenes look at a journey shaped by curiosity, courage, and thoughtful decision-making.

In this conversation, Parker shares:

1. How her early career in lending gave her an “under the hood” view of what truly makes a short-term rental successful—and how she used that insight to build a portfolio spanning the Smokies and Florida’s Panhandle
2. The remarkable story behind acquiring a bona fide Frank Lloyd Wright home in Kentucky, including the family connections and moments of serendipity that led her there
3. What it’s really like to invest during uncertain and unpredictable times, and why balancing solid research with gut instinct allowed her to seize opportunities others overlooked
4. The unique challenges and rewards of restoring and short-term renting a historic home, from navigating appraisals to thoughtfully weaving the property’s history into the guest experience
5. Why putting heart and education above hype—and surrounding yourself with the right community—is essential to building a more meaningful, sustainable business

Parker’s insights and grounded enthusiasm make this episode a must-listen for anyone looking to build a smarter, more intentional vacation rental portfolio. It’s filled with practical takeaways, mindset shifts, and real-world lessons for scaling with clarity and purpose.

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:

1. "It's not always perfect when you're finding properties in the market. So, go and see and feel and trust your gut feeling.”
2. “It's so important that we balance the numbers with our intuition.”
3. “Look ahead of what's coming.”

Let’s Connect:

Website: wealthbuildersmortgage.com

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