The Short Term Show

On this week's episode, Avery is joined by Jamie Folk, a short-term rental investor who owns properties in New Jersey, Maine, and Orlando, Florida. Jamie shares how he acquired an established waterfront rental in Maine that grossed over $100,000 in his first six months of ownership, then purchased a nine-bedroom, themed Orlando vacation home for $980,000 that brought in roughly $70,000–$80,000 in its first few months. He and Avery discuss why Orlando may offer significant opportunities despite concerns about oversaturation, how to stand out with themed bedrooms and standout amenities, and why negotiating on properties that have been sitting on the market can pay off. Jamie also breaks down his experience financing a rental property with an SBA loan, including the lengthy approval process, and explains why he recommends buying an established rental business with a proven track record rather than starting from scratch. Connect with Jamie:  Talley's Corner Properties https://www.airbnb.com/hosting/listings/editor/1438369068791073881/view-your-space https://www.airbnb.com/rooms/1463233960241486611?guests=1&adults=1&s=67&unique_share_id=87228e3a-7279-4ca2-a28c-1800d1939380 https://www.airbnb.com/rooms/1648835351281876391?guests=1&adults=1&s=67&unique_share_id=471021dd-c32d-46bb-80fd-bd9a926a581c Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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 Pam Knudsen of Avalara to break down one of the least exciting but most important parts of running a short term rental: staying compliant with lodging and occupancy taxes. Pam explains why STR tax requirements can vary across states, counties, cities, and special jurisdictions, and why using Airbnb, Vrbo, or a property manager does not necessarily mean all of your tax obligations are being handled for you. She also discusses how jurisdictions are using technology and data to identify unlicensed rentals and unpaid taxes, making compliance more important than ever. Avery and Pam walk through how MyLodgeTax helps owners manage licensing, tax calculations, filings, payments, and renewals, while also covering common mistakes, direct bookings, and what can happen when an owner operates outside the rules. Connect with Pam: https://www.linkedin.com/in/pamknudsen/ https://www.avalara.com/us/en/index.html Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Margot Schmorak, CEO and co-founder of Hostfully, joins the show to discuss how property management software is evolving and what hosts should look for when choosing a PMS. She covers Hostfully’s latest developments in home automation, damage protection, accounting, and AI-powered guest communication, including AI that can handle routine guest questions and flag issues that require a host’s attention. Margot also shares why proper onboarding, configuration, and ongoing management are essential to getting the most out of any software platform, along with her advice for creating a better guest experience and growing a short-term rental business. Connect with Margot: Hostfully.com Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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 Christian Walston, an engineer and real estate investor who turned an accidental introduction to short term rentals into a successful investment in the Orlando market. Christian shares how he went from buying his first long term rental for just $33,000 to purchasing a seven-bedroom vacation rental near Disney, which has already exceeded its conservative first-year revenue projections. He breaks down the property's $700,000 purchase price, $75,000 in theming and game-room upgrades, and why he believes Orlando's reputation for oversaturation is overlooking the market's massive tourism demand. Christian also shares the wild story of a guest discovering a disconnected camera hidden in a bedroom, which temporarily led Airbnb to suspend his listing, and discusses what the experience taught him about documenting issues and having a strong support network. Connect with Christian: https://walstonwindsorhills.directstays.com/ Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Ben Levy, co-founder and CEO of Localbird, to discuss how short term rental hosts can turn local experiences into an additional revenue stream. Ben shares how a frustrating vacation in Hawaii inspired him to build a concierge platform that makes everything from private chefs and massages to tours, transportation, and rentals easier for guests to discover and book. He explains how Local Bird partners with hosts through revenue sharing, integrates with property management software, and uses personalized, timely recommendations to help hosts capture more of their guests’ spending while providing a better hospitality experience. Avery and Ben also discuss why premium properties have an especially strong opportunity to monetize experiences, how AI is making personalized concierge service scalable, and why responding quickly to guest requests can make a major difference in conversions. Connect with Ben: https://www.localbird.com/ https://www.localbird.com/pages/STR-experiences-2026  Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Melissa Nash, founder of Passively Rich with Rentals, to discuss how she built a portfolio of 20 rental properties after starting with just a $15,000 investment. Melissa shares how she uses short-term rentals to make markets like Southern California work, including buying properties that need some attention, turning them into profitable vacation rentals, and even selling them as turnkey businesses. She also explains her “lazy investor” method, why she prioritizes systems and time freedom, and how knowing your target guest can be more valuable than simply trying to maximize the number of people a property sleeps. Avery and Melissa also dive into realistic investment expectations, the importance of understanding your goals, and why consistent “base hits” can build a stronger portfolio than chasing one huge deal. Connect with Melissa: https://www.passivelyrichwithrentals.com/ Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Leslie Carbajal to explore three Arizona short-term rental markets: Sedona, Flagstaff, and Scottsdale. Leslie breaks down what makes Sedona such a compelling luxury market, including its iconic red rocks, strong tourism, limited pool inventory, and potential for higher revenue, while also explaining why Flagstaff offers a more affordable entry point with demand driven by skiing, hiking, and outdoor recreation. They compare the three markets based on price point, property type, amenities, regulations, and traveler demand, with Leslie emphasizing that there is an investment opportunity for nearly every budget. Leslie also shares her personal journey from Short Term Shop client to agent and how Avery's book completely changed her perspective on real estate investing. Connect with Leslie: [email protected] Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Gian Pazzia, one of the founders of KBKG and a longtime expert in cost segregation, to break down how short term rental investors can use tax strategies to maximize depreciation deductions. Gian explains the difference between traditional depreciation and cost segregation, how the short term rental tax strategy can allow qualifying investors to use deductions against active income, and why properly tracking material participation hours is so important. They also discuss the limitations of real estate professional status, what investors should look for when choosing a CPA or cost segregation provider, and how tools like Track750Tax and CostSegregation.com can simplify the process Connect with Gian: kBKG.com https://www.costsegregation.com/  use code: track750STR at track750.tax Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Mary Mueller, a first-time short term rental investor who shares how she and her husband went from feeling priced out of vacation rentals to purchasing and renovating an affordable cabin in the Smoky Mountains. Mary explains how balancing homeschooling, raising three young children, and navigating family health challenges didn't stop them from finding a value-add property, completing a major renovation, and launching a successful rental that has exceeded their early expectations. She discusses the importance of continuous learning, leaning on experienced mentors, and embracing the beginner mindset, while offering an honest look at the challenges of getting a property rent-ready, managing guests, and building confidence as a new investor. The conversation is an encouraging reminder that ordinary families can build long-term wealth through short term rentals with patience, education, and consistent action. Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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 Luke and Laura Hintermeister to share how their family's passion for renovation, hospitality, and outdoor adventure led them to purchase and transform a vacation rental overlooking Lake Superior. The couple explains how years of researching the North Shore market, finding an overlooked value-add property with incredible views, and completing a major renovation themselves helped turn a dated two-bedroom home into a high-performing short term rental. They discuss why buying in a market you know can create a competitive advantage, the importance of focusing on irreplaceable features like location and views, and how involving their children in the renovation has laid the foundation for a family business. Luke and Laura also offer advice for new investors on overcoming the fear of getting started, continually learning the business, and building long-term wealth through thoughtful investing and hospitality. Connect with Luke and Laura: https://lagomescapes.hospitable.rentals Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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