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Discover how ChatGPT can revolutionize your Airbnb business! Learn to optimize your listings for better conversions, enhance guest communication while keeping a hospitable tone, and analyze competitors effectively. Dive into operational efficiencies with AI-generated checklists and smart pricing strategies. Plus, find out how to craft high-converting emails to boost direct bookings. Embrace technology that acts like an extra team member, streamlining your workflow and enhancing guest experiences!

In this Hosting Hotline episode, we tackle a crucial question from host Julia: Should you proactively replace major appliances like HVAC systems and water heaters, or wait until they fail?Julia’s concern is common—her property is 20 years old, and she’s weighing the risk of unexpected breakdowns against the cost of upgrading early. We break down the key factors to consider, including:The hidden costs of running old, inefficient appliancesHow energy efficiency upgrades can save you money in the long runThe potential risks of waiting—guest discomfort, refunds, and emergency repairsA middle-ground approach: inspections, planning, and prioritizing replacementsWhat appliances should take top priority (hint: HVAC failures can be a nightmare)The importance of water monitoring devices and insurance considerationsIf you're a host wondering when to invest in major replacements, this episode will help you make a smart, informed decision that protects your business, your guests, and your peace of mind.Resources:Preventative Airbnb Maintenance: Stop ignoring this or Pay later!! | Subscribe to our YouTube channelAHR | HVAC ExpoMentioned in this episode:Host Checklist | Grab our Airbnb Essentials Checklist and make stocking your Airbnb a breeze – we've got all your hosting needs covered!Proper Insurance | Book Your Risk Assessment Today

In this episode, we sit down with Koryn Okey, Vice President of Community & Engagement at Breezeway, to explore the tools and strategies that can help short-term rental hosts streamline their operations, improve efficiency, and increase revenue.Koryn has been in the vacation rental industry since 2008, starting at FlipKey, where she helped introduce guest reviews to the industry. Now, she plays a key role at Breezeway, helping hosts optimize their businesses through smart automation and operations management.What We Cover in This Episode:How Breezeway Messaging automates guest communication and creates efficiency in your businessThe power of Gap Night messaging and how it can add thousands of dollars to your bottom lineBreezeway’s inventory tracking system and why managing consumables properly can save you moneyBreezeway Assist, a guest messaging solution that frees up your time while maintaining high-quality serviceHow software can help hosts run their businesses more effectively, whether managing one property or a hundredResources Mentioned in Today's Episode:Breezeway | Your first property is free!Breezeway Elevate | A free, two-day event happening on March 11-12The Airbnb Guest Check-In Routine You're Not Doing (And It’s Losing You Money) | Subscribe to our YouTube channelMentioned in this episode:Proper Insurance | Book Your Risk Assessment TodayFido | Visit getfido.com/tfv & get your first month free!Extenteam | Receive 20% off the first 2 months with Tailwind!Hostfully | Go to https://www.hostfully.com/tfv and use TFV100 to get $500 off your subscription.

Getting organized as a short-term rental host can feel overwhelming, especially when you're managing bookings, guest communication, maintenance, and more. In this Hosting Hotline episode, we answer a listener’s question about the best tools and strategies for keeping everything on track—without the stress.We break down how we manage our own Airbnb businesses, from task management software to scheduling maintenance, and share practical tips to help you streamline your hosting operations.What We Cover in This Episode:The best digital tools for Airbnb hosts, including Asana and BreezewayHow to balance property tasks with overall business managementThe power of recurring tasks vs. one-time action itemsWhy your calendar is your best tool for staying on trackHow to audit and update your Airbnb listing efficientlyThe importance of consistency and long-term organization for successResources & Links from This Episode:Asana | asana.comBreezeway | breezeway.io/tfvSubscribe to our YouTube Channel: Exact Steps for Leaving a Negative Airbnb Guest ReviewMentioned in this episode:Host Checklist | Grab our Airbnb Essentials Checklist and make stocking your Airbnb a breeze – we've got all your hosting needs covered!Quiz | Take our quiz to reveal your hosting personality style!

Revenue management is one of the most overlooked skills in short-term rentals, yet it’s the key to maximizing your earnings. Too many hosts rely on guesswork or reactive pricing strategies, leaving money on the table. In this episode, we’re diving into the single most important metric you need to track to confidently adjust your rates and increase revenue: your booking window.Your booking window tells you when guests typically book your property before their stay. Understanding this number allows you to optimize your pricing strategy, adjust in real time, and eliminate last-minute panic.What We Cover in This Episode:Why revenue management is proactive, not reactiveThe difference between bookkeeping and revenue managementWhat your booking window is and why it’s the key to your pricing strategyHow to use the green, yellow, red system to know when to adjust ratesWhy being the first to book can mean you’re underpricingHow to maximize demand and avoid unnecessary discountsThe best ways to pull pricing levers before lowering ratesResources & Links from This Episode:Start optimizing your pricing today | Try PriceLabs FREE for 30 daysSubscribe on YouTube | Boost Airbnb Income with these 4 EASY Upsells!If you’ve been feeling stuck on pricing or unsure when to adjust your rates, this episode will give you the confidence and strategy to take control of your Airbnb’s revenue.Mentioned in this episode:Proper Insurance | Book Your Risk Assessment TodayHostfully | Go to https://www.hostfully.com/tfv and use TFV100 to get $500 off your subscription.Fido | Visit getfido.com/tfv & get your first month free!Extenteam | Receive 20% off the first 2 months with Tailwind!

Hosting Hotline: The Best Pricing Strategy When You First List Your AirbnbWhen you’re launching your short-term rental, pricing can feel like a guessing game. Should you start with low rates to get more bookings and reviews? Or is that a fast track to leaving money on the table? In this Hosting Hotline episode, we answer a listener’s question about how to price their new Airbnb and whether lowering rates is the right strategy.We also touch on midterm rentals—when they make sense, how they differ from short-term stays, and why they are not always the easy alternative some hosts expect.What We Cover in This Episode:Why pricing too low does not always mean more bookingsHow Airbnb already gives new listings a boost in the algorithmThe dangers of relying on lower rates as your default pricing strategyHow to analyze market demand before setting your ratesMidterm rentals vs. short-term rentals—what is the real differenceHow to transition from midterm back to short-term bookings without losing tractionResources & Links from This Episode:Are you a brand-new host? | Get the Hosting Handbook today!Subscribe to our YouTube Channel | Boost Airbnb Income with these 4 EASY Upsells! Would you like us to analyze a specific STR challenge on the podcast? Submit your question at HostingHotline.com for a chance to be featured in a future episode!Mentioned in this episode:Quiz | Take our quiz to reveal your hosting personality style!Host Checklist | Grab our Airbnb Essentials Checklist and make stocking your Airbnb a breeze – we've got all your hosting needs covered!

Why Your PMS is the Heartbeat of Your STR Business—A Conversation with Hostfully’s CEOYour Property Management Software (PMS) is more than just a tool—it’s the heartbeat of your short-term rental business. But how do you know you’re using the right one? And are you truly optimizing it to save time, increase efficiency, and drive more revenue?In this episode, we sit down with Margot Schmorak, CEO & Co-Founder of Hostfully, our preferred PMS partner, to talk about the must-have features of a PMS, the biggest mistakes hosts make when choosing or switching systems, and how to use a PMS to scale smarter—whether you have one property or 100+.We also dive into:The number one mistake hosts make when selecting a PMSHow a strong tech stack can make your hosting life easierDirect bookings: Is a PMS worth it if you only have one or two properties?The power of repeat guests and how a PMS can help you get moreWhy booking direct is one of the biggest opportunities for hosts in 2025How Hostfully’s AI-powered inbox is saving hosts three or more hours per dayHow midterm rentals are evolving—and what Hostfully is doing about itWhether you’re shopping for a PMS, considering a switch, or just want to maximize the power of the one you have, this episode is packed with insights, strategy, and actionable tips to take your STR business to the next level.More About Our Guest: Margot SchmorakMargot is the CEO & Co-Founder of Hostfully, a leading PMS in the STR industry. Under her leadership, Hostfully has helped thousands of property managers streamline their operations, grow their portfolios, and embrace direct bookings as a key revenue driver.Beyond Hostfully, Margot is also a mom, wife, and creative entrepreneur based in San Francisco. She’s passionate about supporting women, moms, and underrepresented groups in tech and hospitality, and she loves travel, design, and music.Resources & Links from This EpisodeListen to Margot’s first TFV EpisodeExact Steps for Leaving a Negative Airbnb Guest Review | Subscribe to our YouTube ChannelWant to get your property featured on #STRShareSunday? | Submit your listing here: strsharesunday.comMentioned in this episode:Proper Insurance | Book Your Risk Assessment TodayHostfully | Go to https://www.hostfully.com/tfv and use TFV100 to get $500 off your subscription.Fido | Visit getfido.com/tfv & get your first month free!Extenteam | Receive 20% off the first 2 months with Tailwind!Quiz | Take our quiz to reveal your hosting personality style!

Which STR Upgrades Actually Increase Bookings?Investing in your short-term rental can be a big decision—so how do you know which upgrades will actually pay off? In this Hosting Hotline episode, we help a listener evaluate whether adding privacy fencing is worth the investment. We dive into when (and why) outdoor enhancements can increase bookings, how to analyze market data before making a major purchase, and what hosts should consider before spending thousands on property improvements.What We Cover in This Episode:How to determine if an upgrade will increase bookings and revenueThe impact of outdoor spaces on guest experience and STR successWhen privacy fencing makes sense—and when it might notHow to use market data to evaluate upgrades before making a decisionWhat amenities can increase perceived value without a huge investmentThe importance of long-term financial planning for property improvementsResources & Links from This Episode:Check out this episode: Design Upgrades That Drive Higher STR Bookings with SomerledSchedule a Call with Somerled Designs: Learn MoreSubscribe to our YouTube Channel: No bookings for your Airbnb? 5 Reasons Why and How to Fix ASAP!Grab your FREE STR Deal Analyzer: Analyze your next deal!Would you like us to analyze a specific STR challenge on the podcast? Submit your question at HostingHotline.com for a chance to be featured in a future episode!Mentioned in this episode:StayFi | Go to www.stayfi.com and enter TFV to get 50% off your first three months.Quiz | Take our quiz to reveal your hosting personality style!

In this episode, we take a deep dive into short-term rental insurance, breaking down why having the right coverage is essential for protecting your property, income, and business. We welcome Nick Massey, Chief Sales Officer at Proper Insurance, who shares critical insights on what hosts need to know, from common misconceptions about platform-provided coverage to real-life case studies of claims and payouts.What We Cover:Why short-term rental hosts need specialized insuranceCommon claims and risks in the short-term rental industryThe differences between standard homeowners insurance, landlord insurance, and commercial policiesHow loss of income coverage can save your business after a claimGuest-caused damage: what’s covered and what’s notHow to ensure your amenities—pools, hot tubs, kayaks, and more—are properly insuredThe biggest mistakes hosts make when it comes to insuranceWhat co-hosts and property managers need to know about liabilityWhy arbitrage hosts need a unique insurance solutionHow insurance providers evaluate your property and listing for risk managementThe importance of transparency when discussing insurance with property ownersResources & Links from This Episode:Breezeway Safety Program | Learn more AirCover for Hosts | Learn more11 Ways To Avoid Parties In Your Airbnbs | Subscribe to our YouTube ChannelMentioned in this episode:Quiz | Take our quiz to reveal your hosting personality style!Proper Insurance | Book Your Risk Assessment TodayExtenteam | Receive 20% off the first 2 months with Tailwind!Fido | Visit getfido.com/tfv & get your first month free!Hostfully | Go to https://www.hostfully.com/tfv and use TFV100 to get $500 off your subscription.

Attending in-person conferences is one of the best ways to network, learn, and level up your short-term rental business—but with so many options, how do you pick the right one? In this Hosting Hotline episode, we help listener Sarah decide which industry event is the best fit for her goals in 2025.We break down the top vacation rental conferences, including their unique focuses, vendor access, educational sessions, and networking opportunities. Whether you're looking for insights on social media marketing, midterm rentals, or revenue management, there’s an event for you.If attending a conference is on your business goals list, listen in for our expert tips on choosing the right one, maximizing your experience, and ensuring your investment pays off.What You’ll Learn in This Episode:How to choose the best short-term rental conference for your goalsThe top STR events in 2025 and what makes them uniqueThe importance of setting a clear objective for attending an eventWhy networking and vendor connections are just as valuable as educationTips for maximizing your experience (and making it a tax write-off)Events Discussed on the Show:Level Up Your Listing – March 9-11, Phoenix, AZ (More Info)VR Nation – April 27-28, Austin, TX (More Info)Midterm Rental Summit – April 27-29, San Diego, CA (More Info)VR Women's Summit – August 19-21, Charleston, SC (More Info)VRMA International – October 12-15, Las Vegas, NV (More Info)DARM (Data & Revenue Management Summit) – December 1-3, Sandestin, FL (More Info)Additional Resources:Meetup.com – Find local real estate and STR networking eventsRentResponsibly.org – Stay updated on local industry events and advocacyMinoan – Meet STR vendors in-person at conferencesListen now to find the best event for your short-term rental business in 2025!Mentioned in this episode:StayFi | Go to www.stayfi.com and enter TFV to get 50% off your first three months.Quiz | Take our quiz to reveal your hosting personality style!