The Short Term Show

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/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]

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 [http://www.therealestatecpa.com/] How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]

On this week's episode, Avery is joined by Yonah Weiss, an expert on cost segregation and a favorite among real estate investors. They break down what a cost segregation study is, how it allows short-term rental owners to accelerate depreciation and save on taxes, and who qualifies to benefit from this strategy. Yonah explains how to navigate bonus depreciation, recapture tax, and 1031 exchanges, emphasizing the importance of having a real estate-focused CPA.    How to connect with Yonah: https://yonahweiss.madisonspecs.com/ [https://yonahweiss.madisonspecs.com/] https://www.yonahweiss.com/ [https://www.yonahweiss.com/] https://www.instagram.com/yonahweiss/ [https://www.instagram.com/yonahweiss/] https://www.linkedin.com/in/cost-segregation-yonah-weiss/ [https://www.linkedin.com/in/cost-segregation-yonah-weiss/] https://twitter.com/YonahWeiss [https://twitter.com/YonahWeiss]   How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]

On this week's episode, Avery is joined by Heather Meuer, a Missouri-based real estate investor who transitioned from running an auto parts business to building and managing RV parks and glamping resorts. Heather shares how she and her husband turned an abandoned campground into a thriving $7.8M resort in Branson, complete with glamping tents, RV pads, a coffee shop, and pizza kitchen—all designed to elevate the guest experience. She walks through the challenges of securing an SBA loan, tips for working with your spouse, and how creating multiple revenue streams can supercharge a hospitality business.   How to connect with Heather: @roaminghomeheather theembersbranson.com   How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]

On this week's episode, Avery is joined by Melissa and Chris Jones, a dynamic investor duo who share how a simple desire for a second home evolved into a thriving short-term rental business and boutique co-hosting company. They walk through their journey from renovating a “turnkey” townhome in Galveston to scaling up with high-performing properties in Broken Bow and Orange Beach. Along the way, they highlight their design strategies, how they stand out in saturated markets, and how word-of-mouth helped them grow a co-hosting portfolio of 25+ properties. Melissa and Chris also offer heartfelt advice for aspiring hosts and share the mindset shifts that helped them go from accidental investors to full-time entrepreneurs.   How to connect with Melissa and Chris: https://bestvacationrentalsever.com [https://bestvacationrentalsever.com/]   How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]