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:

@katiethereattorney
strlaw.com
katiejohnsonplc.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

On this week's episode, Avery is joined by John and Christina McNaught. The couple shares how they transitioned from long-term rentals into short-term rentals after realizing a small Airbnb unit on their property could cover their mortgage and generate additional cash flow. They discuss investing in the Bradenton, Florida market, including seasonality patterns, how being within about 15 minutes of the beach still works for guests, and why understanding the typical “family vacation” guest avatar is critical when designing a property. John and Christina also explain how strategic amenity upgrades like a game room, mini golf, playground, and pickleball court helped turn one property from about $95K in annual revenue into more than $217K.

Connect with an agent: agents@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

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

On this week's episode, Avery is joined by Celeste DiRocco and Philip Pane of Parklin Interiors. They share how they went from buying their first short term rental sight unseen in Gatlinburg to building a six property portfolio across Tennessee, North Carolina, Georgia, and Virginia while designing more than 200 short term rentals nationwide. Celeste explains how thoughtful, ROI focused design choices like strategic accent walls, updated lighting, elevated bedding, and strong exterior appeal can dramatically increase bookings without blowing the budget. They also discuss common investor mistakes, including overspending in the wrong areas, over cramming guest capacity, and going too over the top with themes that can hurt long term resale value. The conversation wraps with insights on enhancing the guest experience, building equity through smart renovations, and why focusing on the right doors instead of more doors can transform your investing strategy.

How to connect with Celeste and Phillip:

https://www.instagram.com/parklin_interiors/
https://www.instagram.com/southern_serenity_stays/

https://parklininteriors.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 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