The Short Term Show

Avery is joined by Katie Johnson, a short-term rental attorney and investor who breaks down the most common legal mistakes hosts make and how to avoid them. She explains key risks like missing deed restrictions, improperly handling LLCs, and failing to secure adequate insurance, along with how to protect yourself from lawsuits tied to pools, amenities, and guest incidents. Katie also dives into service animals vs. emotional support animals, the legal realities of raising capital, and why setting up your business structure correctly from the start is critical. The conversation highlights how being proactive with legal strategy can save investors from costly mistakes down the road. How to connect with Katie: @strlaw.with.katiestrlaw.comkatiejohnsonplc.com How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us 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 Robert Warren, a real estate investor who shares how decades of experience in building, rehabbing, and developing led him to short-term rentals. He breaks down how he transitioned from long-term rentals and flips into STRs, including buying and optimizing properties in Gulf Shores and the Smokies for stronger cash flow and seasonality advantages. Robert also dives into creative deal-making, like using 1031 exchanges and value-add renovations to scale faster, while emphasizing the importance of buying right, avoiding over-leverage, and maximizing guest experience. He wraps with practical advice on investing mindset, building wealth through assets, and using time and skills to create equity early on. How to connect with Robert: detaildesign.biz How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us 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

John McNaught, a Bradenton-area short-term rental investor and agent who shifted from long-term rentals, explains their pivot to high-performing STRs. They discuss Bradenton seasonality and why being ~15 minutes from the beach still attracts family vacationers. They cover choosing island vs mainland goals and how backyard amenities like game rooms, mini golf, playgrounds, and pickleball turned one property into a major revenue winner.

On this week’s episode, Avery is joined by David Taylor. David shares how he transitioned from construction and home inspecting into short term rental investing, ultimately choosing Branson, Missouri for its affordability and strong 10-month tourism season. He breaks down purchasing a brand-new three-bedroom condo for $225,000 and generating nearly $53,000 in gross revenue within his first partial year, highlighting why condos dominate the Branson market and why that can actually be an advantage for out-of-state investors. The conversation also covers financing non-warrantable condos, navigating vacation rental zoning, and why Branson is an ideal entry point for new investors who want solid returns without jumping into a half-million-dollar property. How to connect with David: www.theshorttermshop.com How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us 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

Philip Pane, co-founder of Parkland Interiors and operator of multiple vacation properties, and Celeste DiRocco, designer and co-founder focused on ROI-driven vacation design, share practical STR upgrade tips. They cover high-impact, low-cost changes like paint, lighting, bedding, and curb appeal. They also discuss common investing errors such as overspending, over-cramming capacity, and themed designs that harm resale.

On this week's episode, Avery is joined by Josh Briner. Josh shares how he transitioned from a background in education and flipping distressed properties into building a short term rental portfolio in upstate New York, including the Finger Lakes and Buffalo area. He dives into why he prefers value-add BRRRR deals over turnkey properties, how amenity stacking like pools and saunas can dramatically impact revenue, and what investors should realistically expect during the first year of launching a luxury rental. The conversation also covers scaling a management company to over 100 doors, navigating snow removal and winter challenges, and the mindset required to succeed long term in the hospitality-driven short term rental business. How to connect with Josh: https://www.facebook.com/share/1Cmpm7krpV/?mibextid=wwXIfr https://www.facebook.com/share/g/19kR6UzmSP/?mibextid=wwXIfr  How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us 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 Aubrey Carlson, owner of Salt and Sky Lodging Company and a former military helicopter pilot, to talk about building a short-term rental portfolio in both San Diego and Birmingham, Alabama. Aubrey shares how she used a VA loan and a house-hack-style fixer strategy to break into an expensive coastal market, then expanded into Birmingham with BRRRR-friendly properties that could also perform as short-term and midterm rentals. She also breaks down how she partnered with investors early on—using detailed deal presentations at first, then evolving the structure to properly value rehab labor, design, and ongoing management. Finally, Aubrey emphasizes long-term thinking, choosing strong markets, and leveraging education and community to accelerate portfolio growth. How to connect with Aubrey: www.saltandskylodgingco.com https://www.instagram.com/saltandskylodgingco/ How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 Production done by Outlier Audio

On this week's episode, Avery is joined by Matt Holmes of Get Up North Retreats to explore building a short-term rental business rooted in passion, relationships, and outdoor hospitality. Matt shares how his love of fishing, hunting, and family time led him to pivot from land and off-lake cabins into lakefront rentals—and ultimately into owning and operating a historic Minnesota campground. They discuss why understanding what guests actually want (like lake access), embracing seasonality, and betting on yourself can unlock opportunities even without massive capital. This episode is a powerful reminder that investing in places you truly believe in can create both strong returns and meaningful impact. How to connect with Matt: www.getupnorthretreats.com www.troutlakecampground.com https://www.facebook.com/profile.php?id=61566352371201 https://www.facebook.com/profile.php?id=61574524231835 How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 Production done by Outlier Audio

Kenny Bedwell, founder of STR Insights and short-term rental data analyst, breaks down why the market is stabilizing rather than collapsing. He highlights the widening gap between average and top 10% performers. They cover professionalizing operations, financing pitfalls like overleveraging, strategic asset choices such as one-bedrooms, and how to scale thoughtfully toward top-tier performance.

On this week's episode, Avery is joined by Ross Alcorn, founder of Itinerary Boss, to break down how real estate investors can use credit card strategy to turn everyday spend into serious travel rewards or bottom-line value. Ross shares how his background in sales, real estate investing, and trip planning led him to uncover powerful points strategies—from welcome bonuses to transferable currencies—that most investors completely overlook. They dive into common mistakes like underutilizing Amex points, paying vendors via ACH without earning rewards, and leaving massive value on the table when furnishing or renovating properties. This episode is a practical crash course on leveraging credit cards smarter to fund travel freedom without increasing spending. How to connect with Ross: https://www.instagram.com/itineraryboss https://www.linkedin.com/in/rossalcornru/ https://open.spotify.com/show/1mmMJ6z3JdEOUJKUjLh8bD?si=a0e79b04f3084e68 How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 Production done by Outlier Audio