Short Term Rental Management

On this week’s episode of Short Term Rental Management, Luke shares a candid and unfiltered story about getting fired by a long-term property management company—and the hard lessons that came with it. He walks through red flags like inexperienced managers, poor inspections, inflated rehab estimates, and conflicts of interest, while owning his own mistakes around communication under pressure. The episode serves as a real-world reminder of why vetting managers, setting expectations, and staying involved in asset oversight matter just as much as choosing the right market. How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 Libby of Co Host Oklahoma to unpack what it really takes to scale a co-hosting and property management business to 45+ units. They dive into balancing owner expectations with guest experience, navigating a high-profile $16,000 damage claim, and building scalable systems using tools like Hospitable, PriceLabs and custom automation. The conversation also explores branding, networking, co-hosting vs. property management, and why quality, simplicity, and strong relationships matter more than over-the-top amenities. How to connect with Libby: Website: https://cohostoklahoma.com Direct booking: https://hostlahoma.com Instagram & Facebook: @CoHostOklahoma How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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

David shares his transformative journey from engineering to owning six short-term rentals while managing over 35 for others. He emphasizes disciplined investing, the importance of authentic pricing, and how adaptability is vital in today’s market. The conversation highlights the realities of property management, including building systems and hiring the right team. David discusses his hands-on approach to revenue management and offers insights into his entrepreneurial journey, encouraging freedom over mere financial gain.

On this week’s episode of Short Term Rental Management, Luke explains how short-term rental success often depends on balancing two different mindsets: the creative right brain and the analytical left brain. He breaks down how creative operators excel at design, guest experience, and listings but often struggle with pricing and numbers, while analytical operators thrive on spreadsheets and projections but may overlook presentation and communication. Luke’s key takeaway is that understanding your natural strengths—and intentionally shoring up your weaknesses—is critical to running a profitable, sustainable STR business. How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 breaks down two recent SOP failures—when a deadbolt and backup lockbox both failed—and explains why that kind of catastrophic access breakdown is preventable with better systems. He shares practical fixes like replacing unreliable push-button lockboxes, tracking deadbolt install dates and lockbox details in a spreadsheet, and implementing a semiannual lockbox function test so you’re never scrambling during guest check-in. How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 bookkeeper and real estate investor Ben Day of Lionshare Bookkeeping to demystify bookkeeping for short-term rental owners, from when you actually need a bookkeeper versus just a CPA to what clean books should look like. They dig into pricing for bookkeeping services, the difference between simple landlord books and complex trust accounting for property managers, and the tech stack Ben recommends—including tools like Tally Breeze, Get Clearing, Relay Financial, and QuickBooks Online to streamline STR finances and owner statements. How to connect with Ben: https://lionsharebookkeeping.com/ How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 digs into why you should always assume user error first when guests report that something is “broken,” using real-world examples like HVAC issues and TV/Roku remotes to show how basic property knowledge and calm troubleshooting can save you time, money, and stress. He also talks about why a quick phone call can turn a frustrated guest into a satisfied one, and how presenting yourself as a professional operation (even with just one property) helps you handle problems more smoothly. How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 dives into “The Word Yes” and how a simple mindset shift can dramatically improve your guest experience and reviews. Reflecting on the post-COVID era, Luke explains why hosts can no longer afford to say no to small requests like paper towels or detergent, and how embracing flexibility pays off in long-term success.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 breaks down why he believes “repeat guests are for suckers” and why obsessing over getting people back to the same property is usually a poor use of time. He contrasts the heavy effort of building repeat-guest lists, direct booking systems, and loyalty-style incentives with simply leveraging platforms like Airbnb and Vrbo, which already spend massive amounts on marketing to bring in an endless stream of new guests. Along the way, Luke shares personal stories about travel habits, Disney trips, gas-price frugality, and mindset, all to drive home the point that your house isn’t that special, you’re a landlord first, and your energy is better spent finding new guests than clinging to the same ones.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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 on why nobody will ever care for your property quite like you do. Through stories from his own recent rehab project, he highlights the tension between perfectionism, delegating to contractors, and learning to let go when it comes to rental standards. The takeaway: focus on what matters most and don’t get bogged down by chasing flawless details.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.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