Are creative financing deals the key to unlocking your next short-term rental, or could they lead you into financial trouble? In this episode of Cash Flow Positive, Kenny Bedwell is joined by seasoned real estate investor Brandon Thompson, who has flipped over 2,000 homes and built a diverse portfolio of short-term rentals, long-term rentals, and commercial properties over the past 21 years.

Together, they dive into the real truths behind creative financing in the STR space. Brandon shares his personal experiences with seller financing, Subject-To deals, and owner financing, shedding light on the risks investors often overlook when chasing low-interest deals. He also opens up about pivoting his own portfolio after market saturation and declining returns, and why being intentional with your investments is more important than ever.

If you’re weighing creative financing options or looking to scale your STR business without getting burned, this episode will arm you with practical advice from a veteran investor who’s seen it all. Enjoy!

In This Episode You'll Learn:

• Why creative financing isn’t a “one-size-fits-all” solution
• How to structure seller financing and Subject-To deals the right way
• The hidden risks behind “no money down” deals
• Why the glory days of STR investing are over—and how to adapt
• How to evaluate your return on equity and know when it’s time to pivot.
• The importance of finding the right market and avoiding oversaturated areas
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Strwealthbrokers.com

SouthernCharmVacay.com

Connect with Brandon on LinkedIn

Follow Brandon on Facebook

In this episode of the Cash Flow Positive podcast, Kenny explores unconventional strategies that can open doors for those looking to make significant moves without following the traditional path.

These methods offer flexibility, allowing individuals to bypass common roadblocks while still creating valuable opportunities. However, while these approaches can be highly effective, they also come with unique risks and challenges that must be carefully navigated.

You'll learn how these strategies benefit both parties involved, offering potential advantages that aren’t typically available in standard agreements. By understanding how to structure these arrangements wisely, individuals can maximize their potential while minimizing exposure to unnecessary pitfalls. At the same time, it’s crucial to be aware of the fine print—certain decisions could lead to unexpected consequences if not handled correctly.

Whether you’re new to this approach or simply looking for ways to refine your strategy, this episode will provide valuable takeaways you won’t want to miss.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today!

Enjoy!

In This Episode You'll Learn:

• Creative financing for STRs, and how it allows direct negotiations with sellers, creating custom terms without the extensive paperwork required by banks.
• The concept of subject-to financing, where the seller assigns their mortgage to the buyer.
• Owner financing, a method popular with sellers who don't need immediate cash and want to avoid taxable events from selling.
• The risks associated with creative financing, including the potential for banks to call the loan if they discover the deed change.
• And much more...

In this episode of the Cashflow Positive podcast, Kenny is joined by Josh Briner, owner of Vibe Short Term Rental Management.

During the conversation, Kenny and Josh emphasize the importance of putting your best foot forward from the start, surrounding yourself with knowledgeable professionals, and making data-driven decisions. They highlight how working with industry experts, leveraging the right tools, and carefully crafting an experience tailored to a target audience can make all the difference.

You'll learn the value of looking beyond surface-level costs and considering long-term gains. A conservative but intentional approach to investing in quality can lead to higher returns and a competitive edge. By understanding market demand and focusing on key differentiators, individuals can set themselves apart in an increasingly crowded space.

This episode shows that, with a strong foundation and a willingness to adapt, even seemingly daunting landscapes can become profitable and rewarding.

If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!

Enjoy!

In This Episode You'll Learn:

• The challenges of managing properties near sports stadiums, such as the Buffalo Bills' stadium.
• Why Josh advises investors to focus on areas with established regulations and to work with experts who understand the local market.
• How small improvements, like adding a barrel sauna, can significantly increase revenue.
• The future of short-term rental investing in New York, taking into consideration new regulations and taxes.
• And much more...