Short Term Rental Management

On this week’s episode of Short Term Rental Management, Luke welcomes Tim Grillot back to the show—a real estate investor, car enthusiast, and now vacation rental photographer—who shares his journey from corporate life to STR ownership and creative entrepreneurship. They dive deep into the evolution of Airbnb photography, the technical side of staging and lighting, and how Tim and his wife are helping STR owners showcase their properties through immersive, guest-focused imagery. The episode also touches on vacation-town living, hospitality mindsets, and why answering your phone can set you apart.    Check out Scroll Stopper Photography: scrollstopperphotography.com    How to connect with Luke: The Short Term Shop - https://theshorttermshop.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 of Short Term Rental Management, Luke chats with Jeremy Udovich of Sheboygan Vacation Rentals, who’s building a thriving short-term rental business in Wisconsin while still working full-time in tech. Jeremy shares how he and his sister grew from one property to a co-hosting portfolio of 19 units—without burning out. They discuss automation, working with family, market seasonality, and the importance of hospitality (including the golden rule: “give them the pickle”). Jeremy’s measured, sustainable approach to growth highlights how keeping your day job can actually accelerate real estate success.    How to connect with Jeremy: sheboyganvacationrentals.com   How to connect with Luke: The Short Term Shop - https://theshorttermshop.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 of Short Term Rental Management, Luke is joined by Rubin Horowitz, founder of STR Super Cleaners, a rapidly growing short-term rental cleaning company operating in multiple U.S. markets. Rubin shares how he scaled from solving his own cleaning headaches in the Poconos to managing over 700 properties across markets like the Smokies, Emerald Coast, and Nashville. They dive deep into automation, team building, property maintenance support, and how his company partners with hosts and managers while steering clear of full property management. Reuben also offers tips for creating five-star guest impressions—like integrating welcome screens and maintaining scent standards.   Visit strsupercleaners.com to request a quote or consultation   How to connect with Luke: The Short Term Shop - https://theshorttermshop.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 of Short Term Rental Management, Luke is joined by Short Term Shop Plus coach Chuck Kramer to discuss whether it's appropriate for Airbnb cleaners to request tips. Both Luke and Chuck come out in favor of allowing tipping—drawing from their personal experiences in hospitality—but agree that leaving tip envelopes labeled “The Management” crosses a line into tacky. They emphasize that subtle, respectful options (like countertop signs or guidebook mentions) are a better alternative for encouraging gratuity without pressuring guests.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.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 of Short Term Rental Management, Luke reflects from New Orleans on the changing tides in real estate investing and pays tribute to personal heroes Ozzy Osbourne and Hulk Hogan. He shares updates on a new beach house rehab project and emphasizes that while real estate is currently “not cool,” that perception presents an opportunity for disciplined investors. Luke argues that public sentiment, not interest rates, is the real market barrier—and encourages listeners to stay persistent, find motivated sellers, and act before the market becomes “hot” again.     How to connect with Luke: The Short Term Shop - https://theshorttermshop.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 of Short Term Rental Management, Luke is joined by guests Jeff and Jenny, first-time short-term rental investors who share their journey of overcoming a major challenge: their well running dry just months after purchasing a Smoky Mountain cabin. The couple recounts navigating the emotional and financial stress, installing a 1,000-gallon water storage system, and maintaining a positive mindset through it all. They also discuss what they’ve learned about resilience, systems, and generational wealth.    How to connect with Luke: The Short Term Shop - https://theshorttermshop.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 of Short Term Rental Management, Luke Carl shares a personal milestone—he’s selling one of his vacation rental homes. He opens with a humorous tale about replacing a toilet valve himself, then dives into the reasoning behind the sale, including shifting family preferences, property management logistics, and market timing. Luke reflects on pricing strategy, buyer behavior, and current real estate trends, emphasizing that sellers need to be realistic in 2025's slower market.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.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 of Short Term Rental Management, Luke sits down with Miles from Hospitable for an in-depth discussion on the evolution and current state of property management software. They cover Hospitable’s recent dynamic pricing launch, AI-powered tools like the Knowledge Hub and Copilot, and how sentiment analysis is flagging guest issues in real time. The conversation also touches on the growing momentum behind direct bookings and the future of PMS as a “short-term rental super app.”    How to connect with Luke: The Short Term Shop - https://theshorttermshop.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 of Short Term Rental Management, Luke takes listeners through a string of recent challenges he faced in the world of property ownership—from termites and fire damage to a $46,000 miscommunication with a vendor. He walks through seven issues in total, including an inherited tenant move-out requiring a full unit renovation, a fragrance-sensitive guest, and a collapsing porch post that turned out to be decorative. Through it all, Luke emphasizes the importance of communication and staying resilient as a property owner.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.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

Dive into the world of short-term rental management as critical mistakes are laid bare. Discover the dangers of rushing into deals and the art of patient investment. Learn how essential clear communication can transform guest experiences and set expectations right. Dive deep into financial pitfalls that every owner should avoid, and understand how organization can pave the way for success. This is a reality check for anyone looking to thrive in the rental market!