The Airbnb Taxes You Likely Don't Know About

Your Next Booking is Coming From ChatGPT

AI is changing the way travelers discover short-term rentals—and it’s happening faster than most hosts realize. In this episode, Mark Lumpkin sits down with Gil Chan, Founder & CEO of Crafted Stays, to discuss how AI search, direct bookings, and modern website strategies are reshaping the future of the STR industry. Gil explains why relying solely on OTAs is becoming increasingly risky, how AI platforms like ChatGPT and Gemini are influencing guest booking behavior, and what hosts can do today to position their properties for the next generation of search. He also shares how Crafted Stays is helping operators build high-converting direct booking websites that are optimized for both traditional SEO and AI-powered discovery. Whether you're managing one property or hundreds, this conversation is packed with practical insights to help you future-proof your business. In this episode, you'll learn: *  Why AI is changing how guests search for vacation rentals  *  How direct bookings compound over time while OTA bookings stay transactional  *  The importance of identifying your ideal guest avatar  *  What SEO, AEO, and GEO mean—and why they matter  *  How to build a website that's ready for the future of travel search  *  Why hospitality and guest experience still matter more than ever  If you're serious about growing your direct bookings and staying ahead of where the industry is headed, this is an episode you won't want to miss.

Monday Market Data: Breakdown of Asheville, NC Amenities Market

In this week's Monday Market Data Report, Mark Lumpkin breaks down the short-term rental market in Asheville, North Carolina, combining revenue by bedroom count with amenity data to show investors exactly where the biggest opportunities are. Despite the challenges following Hurricane Helene, Asheville continues to be one of the country's fastest-growing mountain destinations, welcoming millions of visitors each year and showing strong signs of recovery. In this episode, you'll learn: * How revenue changes by bedroom count * Why 5 and 6-bedroom properties dramatically outperform smaller homes * Which amenities are becoming must-haves * How to differentiate your property from the competition The data shows: • Fire Pits → 71% of listings • Hot Tubs → 53% • Game Rooms → 24% • Saunas → 11% • Pools → 5.5% • Pickleball & Mini Golf → Less than 2% The takeaway? A fire pit and hot tub help you compete. Adding amenities like a sauna, pool, pickleball court, or mini golf is how you create a true standout property. If you're considering investing in Asheville, this episode provides a data-driven blueprint for building a top-performing STR. Subscribe for new Market Data Reports every Monday and expert guest interviews every Friday.

The Airbnb Taxes You Likely Don't Know About

Most short-term rental owners assume Airbnb and Vrbo handle all of their lodging taxes. They don't. In this episode, Mark Lumpkin sits down with Julie Banting Rogers from Avalara to uncover one of the biggest blind spots in the STR industry: lodging tax compliance. Julie explains why thousands of hosts and property managers unknowingly fall out of compliance, how platform-collected taxes actually work, and why failing to file the right paperwork can result in massive penalties, interest, or even liens on your properties. In this episode, you'll learn: *  How Airbnb and Vrbo handle lodging taxes (and what they don't do)  *  The difference between state, county, and local lodging taxes  *  Why many STR operators unknowingly owe back taxes  *  The costly mistakes property managers make  *  How to stay compliant without spending hours on paperwork  *  What every STR owner should know before buying their next property  If you own, manage, or are planning to invest in short-term rentals, this episode could save you from an expensive mistake. __ Episode Sponsored By: STR Search STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com [http://strsearch.com/]

Monday Market Data: Breakdown of West Palm, FL Amenities Market

In this week's Monday Market Data Report, Mark Lumpkin breaks down the short-term rental market in West Palm Beach, Florida, combining bedroom-count revenue data with amenity-stack analysis to show investors exactly where the biggest opportunities exist. West Palm continues to see strong tourism growth, with more than 10 million annual visitors and growing demand fueled by major corporate relocations from cities like New York, Philadelphia, and Washington D.C. In this episode, Mark covers: • Revenue potential by bedroom count • Why 4, 5, and 6-bedroom homes dramatically outperform smaller properties • The amenity combinations driving $200,000+ annual revenue • What amenities are becoming mandatory in the market • How investors can still stand out from the competition Key takeaways: * 4-bedroom properties average over $100K annually * 6-bedroom properties average more than $200K annually * Top performers can exceed $300K+ per year * Pool + Hot Tub + Waterfront is the highest-performing amenity combination * Only 4% of properties have pickleball courts * Less than 1% have movie theaters If you're investing in South Florida, this episode provides a roadmap for building a high-performing STR that stands out in a growing market. Subscribe for new Market Data Reports every Monday and expert guest interviews every Friday.

28 Years in the Hospitality Industry

What does it take to stay relevant in the short-term rental industry for nearly three decades? In this episode, Mark Lumpkin sits down with Michael St. Pierre, a hospitality veteran with 28 years of experience spanning vacation rentals, luxury resorts, revenue management, owner acquisition, and some of the industry's most recognized brands. Michael shares how he got started in the business, the lessons he learned from working in Hawaii and with Hyatt-affiliated properties, and why hospitality is still the foundation of long-term success in a rapidly changing industry. They also discuss: • What investors can learn from luxury hotel brands • Why relationships are one of the most valuable assets in business • The evolution of revenue management and dynamic pricing • How AI is changing the vacation rental landscape • The importance of building systems, standards, and memorable guest experiences • What the next generation of STR operators needs to focus on Whether you manage one property or hundreds, this conversation is packed with practical insights on hospitality, growth, and building a sustainable business in the vacation rental industry. Connect with Michael St. Pierre on LinkedIn to learn more about revenue management, owner acquisition, and the future of short-term rentals. 🎧 Listen now and be sure to subscribe for more STR Investing Podcast episodes. __ Episode Sponsored By: STR Search STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com [http://strsearch.com/]