On this week's episode, Avery is joined by Tammy Gibbons, who shares how she and her husband transformed their 120-acre Wisconsin family farm into a thriving short-term rental business through a 1031 exchange. Tammy discusses how they landed on Panama City Beach as their market, the decision to self-manage while balancing full-time careers and parenting, and why condos—despite the stigma—ended up being the right investment. She also dives into how systems, communication, and intentional habits have helped her stand out and succeed, grossing $200K annually from two beachfront condos.

How to connect with Tammy:

www.enjoytheviewstr.com

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode, Avery is joined by Taylor Jolly, founder of Roam Free Vacation Home Rentals, to discuss how he transitioned from construction project management to profitable real estate investing. Taylor shares how he’s made co-living and large short-term rentals cash flow in expensive markets like Austin, leveraging creative strategies like hard money loans and wholesaler deals. He also explains how his hospitality-focused brand Roam Free helps other investors find, design, and manage standout STRs in the Texas Hill Country. From poker sheds to above-ground pools, Taylor’s story is a great reminder that there’s more than one way to win in real estate.

How to connect with Taylor:

https://roamfreevhr.com/
https://www.instagram.com/roamfreevhr/

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode, Avery is joined by Brandon Hall and Nathan Sosa of Hall CPA to dive deep into the short-term rental tax loophole and how investors can legitimately use it to offset W2 and business income. They discuss the origins of the loophole, how to qualify through material participation tests, and what documentation is necessary to survive an IRS audit. The conversation also covers depreciation recapture, bonus depreciation updates, and common traps tax influencers don’t warn you about. Whether you’re an investor with one STR or 100, this is a must-listen for anyone trying to minimize taxes the right way.

How to connect with Brandon:

https://www.linkedin.com/in/brandonhallcpa/
https://www.facebook.com/realestatecpa
https://x.com/TheRECPA
www.therealestatecpa.com

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon