The Short Term Show

On this week’s episode of The Short Term Show, Avery interviews Karlton Dennis. The two dig into how the short-term rental tax strategy actually works today, including what “material participation” really means in an audit. They cover using cost segregation and (current) bonus depreciation to create paper losses, the do’s and don’ts of hour-tracking, and smart Q4 timing for acquisitions. Karlton also shares pitfalls that trigger audits and when condos do (or don't) make sense.     How to connect with Karlton:  https://taxalchemy.com/https://www.instagram.com/taxalchemyadvisors/https://www.instagram.com/karltondennis/ 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 Andrew Llewellyn to unpack how he built a thriving short-term rental business in Louisville, KY. He shares the pivot from an almost-bakery to 10–30 guest stays, the data-driven playbook behind tiered calendar openings and last-minute pricing using throughput accounting, and why in-house cleaning and EOS/Traction keep operations tight. Andrew walks through converting an 18,000-sq-ft office into eight 4-bed/2-bath units (projected $800–$900k gross) after a first 10,000-sq-ft building that now grosses ~ $400k, plus the realities of SBA 504 financing (six–eight months and 40 bank conversations). Tech stack highlights include Guesty, PriceLabs (with manual event overrides), RemoteLock, and a heavy weekly metrics cadence.    How to connect with Andrew:  https://superstaysstr.com/https://andrewllewellyn.com/@iamandrewllewellyn 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

Brenna Carles, an expert in mortgage rates and the real estate market, shares her insights from leading Mortgage Shop. She discusses the impact of Powell's recent messaging on mortgage rates and what it means for investors. Brenna explains why lenders pre-price ahead of Fed meetings, and how economic indicators like the 10-year Treasury and inflation flow into rate sheets. She also highlights strategies for refinancing and using seller credits to create better financing options in today's market.

On this week's episode, Avery is joined by Jae Seok An, founder of Airbtics, to dig into smarter market selection and the realities of STR data. They walk through Airbtics’ draw-your-own-market mapping, listing density by bedroom count, and the Market Explorer—tools aimed at helping newer investors compare many locations, budgets, and regulation profiles quickly. Jae shares where the platform is headed (more granular property-level history, clearer “active listing” definitions, and global coverage) and offers practical takes on saturation, accuracy, and why your operations can double or triple revenue on the same property. He closes with advice to start with free analytics, research multiple markets, and then narrow to neighborhood-level decisions. How to connect with Jae: airbtics.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 Rashmi Bhat. Rashmi shares how she went from opening a restaurant at 21 to falling in love with Airbnbs, quickly building a multi‑market STR portfolio and scaling management in the Texas Hill Country to dozens of units through systems and a VA team. She and Avery dig into why the Hill Country still has room for standout properties—and the realities (like taxes) investors should underwrite—plus how keeping a W‑2 can be a strategic “fortress” while you grow cash‑flowing assets.    How to connect with Rashmi: Toasty Indian on socials   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 Wayde Hall from the Short Term Shop for a hands-on walkthrough of how he uses Price Labs Market Dashboards to analyze properties in detail. Wayde demonstrates step-by-step how to filter for specific property types, review counts, and amenities, then sort by revenue to identify top performers and pinpoint areas for improvement. He shows how to spot seasonality trends, set realistic pricing expectations, and understand which amenities or policies impact booking rates. The episode is packed with actionable tips for both beginner and seasoned investors who want to get beyond surface-level data and make smarter STR decisions.   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

Wayde Hall, a Short Term Shop agent in the Smoky Mountains, shares his expertise in short-term rental analysis using Price Labs Market Dashboards. He reveals how granular data—like occupancy rates and cleaning fees—can uncover performance patterns that broad averages miss. The conversation covers strategies for comparing neighborhoods, selecting top-performing properties, and avoiding common pitfalls in data interpretation. Wayde also offers valuable tips for new users, ensuring they focus on impactful filters for smarter investment decisions.

In this conversation, Bobby Birch, a successful real estate investor who grossed $98K in his first year with a short-term rental in the Smoky Mountains, shares his journey. He discusses navigating high interest rates and how thoughtful amenities helped him earn 127 five-star reviews. Bobby reveals tips on spotting hidden gems in the market and emphasizes the importance of guest experiences and personalized service. He also offers financial strategies, including using a 5/1 ARM refinance to boost profitability while standing out in a competitive hospitality scene.

Adrienne Green, a real estate investor and full-time traveler, shares her journey from teaching to creating a successful short-term rental business. She discusses how she transformed her local rentals into a remote management system using virtual assistants. Adrienne highlights the importance of strong SOPs and tech tools like Monday.com for efficiency. She also offers insights into the financial intricacies of investing in rental properties while traveling the world with her family, proving that real estate can empower a flexible lifestyle.

In this engaging discussion, Barbara Schreihans, founder of Your Tax Coach, spills the secrets on maximizing tax savings for real estate investors focusing on short-term and mid-term rentals. She highlights how to harness the short-term rental loophole and when to transition to mid-term rentals for optimal advantage. Barbara shares practical audit-proofing strategies, common tax prep pitfalls, and the significance of choosing the right tax professional. Tune in for insights that could transform your real estate investment approach!