The Short Term Show

On this week’s episode, Avery is joined by Tamara Brown. Tamara shares how she stumbled into real estate while caring for her grandparents, turning multiple family homes into rentals before purchasing her first STR in Destin, Florida. She explains how she analyzed her numbers, leaned on mentorship, and embraced the “enemy method” to size up competition. Tamara also talks through condo ownership fears, financing through a family sale, and why fear should never stop you from pursuing real estate opportunities.   How to connect with Tamara:  HELLOSUNSHINE.BIZ 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

On this week’s episode, Avery is joined by Amy Morehead. Amy shares how turning a family chalet in the Smokies into an STR during her mother’s Alzheimer’s caregiving season sparked a value-add strategy focused on “hot-mess” properties, smart renovations, and self-management. She explains why high-impact finishes beat flashy amenities for appraisal value and how she hunts deals with high days-on-market near the Smokies and along Kentucky’s Bourbon Trail. Amy also talks numbers, the refi-later mindset, and the education-plus-mentorship approach that helped her triple revenue after taking management in-house.   How to connect with Amy:  https://mapleleafpromise.com/https://strfixitpros.com/https://www.facebook.com/Strfixitpros/@STRFIXITPROS 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

In this conversation, Annie Lee, co-founder of Hello Host and a seasoned short-term rental operator, explains how their AI platform automates guest communications seamlessly. She shares insights on how the AI learns from past interactions, makes judgment calls on guest issues, and emphasizes the importance of maintaining a human touch in hosting. Annie also discusses the future of AI in the industry, practical tips for evaluating AI vendors, and her journey in the tech startup world, providing valuable advice for hosts looking to enhance their guest experience.

Karlton Dennis, a licensed enrolled agent and founder of Tax Alchemy, shares his expertise on real estate tax strategies for investors, focusing on short-term rentals. He explains material participation rules and how they impact audits. The discussion includes leveraging cost segregation and bonus depreciation to generate paper losses, misconceptions about hour-tracking, and the timing of acquisitions. Karlton also highlights common audit pitfalls and when investing in condos makes sense, providing valuable insights for savvy property owners.

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.