390. Hosting Hotline: How Do I Transition from Short Term to Midterm Rentals During the Winter Season?

We’re thrilled to welcome Alexa Nota and Dave Krauss, co-founders of Rent Responsibly. Rent Responsibly is a community building and education platform on a mission to support short-term rental operators. They bring people in the STR community together, promote fair and reasonable regulation, and give hosts the tools they need to advocate for themselves. One of those tools is the new State Of The STR Industry Report, a comprehensive look at the latest data and trends on STR hosts and managers, tech, regulations, and local policy. In today’s episode, we do a deep dive into the report and all the lessons you can take away from it. We talk about the report’s most surprising findings, common misconceptions about STRs, and how to get involved in your local government to make your voice heard on housing ordinances. Alexa and Dave shed light on the most common challenges STR hosts face — plus the biggest win-win opportunities. This enlightening conversation makes us even more excited about the future of the hosting industry.(00:01:08) #STRShareSunday: @the.bungalow.butlers(00:05:28) Introducing Rent Responsibly (00:09:05) The State Of The STR Industry (00:15:01) The Report’s Most Surprising Findings (00:21:46) Why STRs Are About More Than Money (00:31:56) How To Stay Updated On Your Local Ordinances (00:34:02) The Biggest Challenges STR Hosts Face(00:38:00) What Hosts Can Do To Move The Mission Forward (00:46:51) How To Create Your Own Marketing Buzz Resources:• Click here for full show notes • Rent Responsibly: rentresponsibly.org• Get the State Of The Industry Report: rentresponsibly.org/2024-sstri/• Learn more about Brumby McLeod, PhD: thanksforvisiting.com/podcasts/363/• #STRShareSunday: @the.bungalow.butlers• Submit your property for our next #STRShareSunday at strshare.com• Video: Every Airbnb Host NEEDS These House Rules• Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned in this episode:Superhog | Visit superhog.com/thanks-for-visiting and book your FREE demo today!

Welcome back to the Hosting Hotline! This is an Ask Me Anything where each week we’ll answer your questions on Airbnb, STRs, real estate, and everything in between.Diana asks:I am trying to furnish my first Airbnb, and I'm in the throes of figuring out which mattress to choose. You mentioned a hybrid, and I can't find links to the one you recommend. What do you suggest? (00:02:59) The Hybrid Mattresses We Use & Recommend • Helix Hospitality Mattress from HostGPO• Why HostGPO is worth the investment • Lucid Mattress from Amazon (00:04:39) Advice For Choosing Linens • Why linens are just as important as the mattress itself • The pros of standard textile linens(00:05:30) Handy Resources For Airbnb Hosts • Hosting Handbook• Airbnb Essentials ChecklistThanks to everyone who submitted questions. To hear your voice on the show and send a question to Sarah and Annette, submit your burning hosting questions at: hostinghotline.com.Resources:• Click here for full show notes • Helix Hospitality Mattress from HostGPO: members.hostgpo.com/users/apply/?via=0755e5• Lucid Mattress: amzn.to/3yK6GwL• Video: The Best Airbnb Bedding For Your Guest • Hosting Handbook: thanksforvisiting.com/handbook• Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned in this episode:Join us for a Damage Waiver Crash Course: thanksforvisiting.com/courseStayFi | 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!Hosting Handbook | Get everything you need to fast track your way to Superhost at thanksforvisiting.com/handbook

Today, we’re excited to pass the mic to one of our longtime Hosting Business Mastermind members, Tanya Rooney. Tanya interviewed us for her podcast, Tribe Builders, and we’re sharing the full conversation here. Through our Hosting Business Mastermind, Tanya found her tribe in the short-term rental space. The women she met in the mastermind helped inspire her real estate, business, and personal growth. In this episode, we talk about the importance of community in buying and running short-term rentals. We give advice on how to build and nurture community through online engagement and in-person events. We also share our biggest surprises, wins, and misses in building our business. And we get real about the limiting beliefs that we’re still working through — and how they will fuel our next steps. If you’re ready to find your tribe in the short-term rental space, this episode is a must-listen! (00:01:08) #STRShareSunday: @elranchitopoconos(00:04:08) Introducing Tanya Rooney (00:07:44) Tanya Interviews Us! How We Built A Community Around Short-Term Rentals (00:16:59) Nurturing Community Through Online Engagement & In-Person Meet-Ups(00:24:42) Building & Choosing Community With Intention (00:28:27) The Biggest Surprises Of Our Community Building Journey (00:37:47) Overcoming Self-Limiting Beliefs (00:44:26) Leaning On Your Tribe (00:50:22) Our Biggest Wins & Misses (00:55:42) What We’re Looking For Right Now Resources:• Click here for full show notes • #STRShareSunday: @elranchitopoconos• Submit your property for our next #STRShareSunday at strshare.com• Hosting Business Membership: https://thanksforvisiting.com/join• Tribe Builders Podcast: tanyarooney.com/podcast• Video: 10 Beginner Steps To Setting Up Your Airbnb Business • Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned in this episode:Superhog | Visit superhog.com/thanks-for-visiting and book your FREE demo today!Host Checklist | Grab our Airbnb Essentials Checklist and make stocking your Airbnb a breeze – we've got all your hosting needs covered!Minoan | Visit MinoanExperience.com and tell them TFV sent you!Join us for a Damage Waiver Crash Course: thanksforvisiting.com/course

Welcome back to the Hosting Hotline! This is an Ask Me Anything where each week we’ll answer your questions on Airbnb, STRs, real estate, and everything in between.Vanessa asks:I have a pet-friendly apartment on 5 acres in rural Florida and added 7 wildlife warnings to my welcome book. Is this too much information, or is it better to warn guests about potential risks?(00:01:42) The Importance of Providing Clear & Concise Safety Information to Guests• Validating the intent of providing warnings and being guest-centric• Safety is always essential when providing information to guests!(00:03:43) Advice for Providing Nature Warnings• Our advice for providing nature warnings for guest pets and children• How you can address this warning in multiple places(00:05:08) Unique & Memorable Ways to Share Important Information with Guests• Memorable ways to inform guests of important warnings• How to inform guests about safety in a fun way• Pet-Friendly Airbnb Listings: Welcoming Dogs to Your Short-Term Rental (Episode 335)(00:06:41) Making Messaging Clear, Positive & Visible• Highlighting nature as a feature of your property in a positive way• The importance of visual warnings in different areas of the property for all guests • Reference the National Park Service for inspiration on messaging (00:08:23) Don’t Be Afraid to Ask for Feedback!• How to ask your guests for feedback about this updated messaging• Building rapport with guests and knowing who might be receptive to sharing feedbackThanks to everyone who submitted questions. To hear your voice on the show and send a question to Sarah and Annette, submit your burning hosting questions at: hostinghotline.com.Resources:• Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned in this episode:Hosting Handbook | Get everything you need to fast track your way to Superhost at thanksforvisiting.com/handbookQuiz | Take our quiz to reveal your hosting personality style!StayFi | Go to www.stayfi.com and enter TFV to get 50% off your first three months.

Curious about what's going on behind our latest investment in the 134 acres of Hocking Hills? We’re diving into why we told our construction team to stop, how we're preparing to approach private money lenders, and the fun (and challenges) we’re facing with this glamping project. We also discuss how we approached working with someone to create financial models, lessons learned, and our next steps. We can’t wait to see how this project unfolds and catch you up again soon!(00:01:08) #STRShareSunday: @thecliffs_hockinghills(00:04:29) Project Update: What’s Going on At Our Hocking Hills Investment Property(00:16:24) Growing Pains & Lessons In Team Communication(00:23:16) Progressing The Project Forward with Financial Modeling(00:33:09) The Reality of Balancing Time & Finances & Why You Should Check Your Insurance PolicyResources:• Rich Hollow Retreat Instagram: @richhollowretreat• #STRShareSunday: @thecliffs_hockinghills• Submit your property for our next #STRShareSunday at strshare.com• Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned in this episode:Superhog | Visit superhog.com/thanks-for-visiting and book your FREE demo today!Hosting Handbook | Get everything you need to fast track your way to Superhost at thanksforvisiting.com/handbookHost Checklist | Grab our Airbnb Essentials Checklist and make stocking your Airbnb a breeze – we've got all your hosting needs covered!

Welcome back to the Hosting Hotline! This is an Ask Me Anything where each week we’ll answer your questions on Airbnb, STRs, real estate, and everything in between.Delilah asks:How do I address concerns with property owners who constantly monitor security cameras and update me on guests' activities, without offending them or jeopardizing our working relationship?(00:01:03) Delilah Asks: How Do I Tell The Property Owners to Stop Checking Security Cameras?(00:02:31) How to Communicate the Importance of Guest Privacy with Owners• How Sarah has communicated with owners about this issue in the past• Explaining why guests deserve privacy and how to set this boundary(00:04:31) Setting Up Proper Channels for Communicating with the Property Owner• Addressing owners texting about property management• Setting processes in place for how the property owners can communicate with you • Why we don’t give out our personal cell phone numbers• Channels we use for communication• RingCentral• Grasshopper(00:07:29) Adding A Guest Privacy Clause to Your Contract• Considering how your guests are more like you than you think • Adding a clause in your contract about behavior if the property has a Ring camera Thanks to everyone who submitted questions. To hear your voice on the show and send a question to Sarah and Annette, submit your burning hosting questions at: hostinghotline.com.Resources:• Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned in this episode:StayFi | Go to www.stayfi.com and enter TFV to get 50% off your first three months.Hosting Handbook | Get everything you need to fast track your way to Superhost at thanksforvisiting.com/handbookQuiz | Take our quiz to reveal your hosting personality style!

Today, we're excited to welcome back a familiar face, Colleen Prochaska, a key player in our property management team, managing everything from guest services to revenue management. In this episode you’ll get a peek inside our in-depth quarterly meetings where we review how things are going and where we're headed in our short term rental business.In this episode, we'll be diving into the past three months of key performance indicators, reviews, and team dynamics, as well as forecasting strategies for the next three to six months, sharing key strategies for property management and business growth along the way. We share insights on what we’ve learned leading virtual teams, how we optimize revenue through data-driven decisions, and adjust strategies for better occupancy. We also discuss our customer service expectations, and how Colleen wonderfully handles guest communication and feedback. Finally, we take a look at how we are preparing for seasonal shifts. If you feel lost or intimidated by the analytics side of your short term rental business, this episode will be your guide to leveraging data to grow your business! (00:01:27) #STRShareSunday: @apex38655(00:03:54) How to Train, Lead & Empower a Virtual Team(00:10:45) Tackling KPI’s: Behind The Scenes Of A Revenue Growth Meeting(00:17:19) Midhoff Property Review: Booking Window, Occupancy & Revenue Optimization(00:24:43) Eastview Property Review & Advice for Getting Comfortable with Revenue Management(00:35:43) Tracking Numbers 101 & Our Strategy for Filling Gap Nights(00:39:25) Going Over Reviews! Handling Constructive Criticism & Responding to Guest Feedback(00:47:42) How We’re Forecasting for the High Season & Preparing for the Low SeasonResources:• #STRShareSunday: @apex38655• Submit your property for our next #STRShareSunday at strshare.com• Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned in this episode:Minoan | Visit MinoanExperience.com and tell them TFV sent you!Hosting Handbook | Get everything you need to fast track your way to Superhost at thanksforvisiting.com/handbookHost Checklist | Grab our Airbnb Essentials Checklist and make stocking your Airbnb a breeze – we've got all your hosting needs covered!Superhog | Visit superhog.com/thanks-for-visiting and book your FREE demo today!

Welcome back to the Hosting Hotline! This is an Ask Me Anything where each week we’ll answer your questions on Airbnb, STRs, real estate, and everything in between.Matthew asks:Should I switch to a midterm rental strategy to address our slow winter season and if so, what’s the best website for leads? How can I protect my property against potential squatters?(00:01:36) Hosting Hotline Success Story Highlight• Youtube: Parent Child Listing(00:03:10) Matthew Asks: Should I Switch to a Midterm Rental Strategy?(00:03:41) Our Experience with Transitioning from A Short Term to Midterm Rental Strategy• Where we find our leads: Furnished Finder, AirBnB, Zillow, ALE and CRS• Pros and cons of using Furnished Finder• Considerations and questions to consider with a midterm rental• Advice for negotiating pricing in a furnished midterm rental(00:09:06) How to Prepare Your Listing for This Rental Strategy Transition• When to start advertising for the winter season• When to take a listing off the market(00:12:21) How to Navigate the Algorithm To Increase Leads on AirBnB(00:13:30) Protect Your Property Against Squatters: Advice for Midterm Rental Agreements• What to look for to prevent a tenant from becoming a squatter• How to protect yourself in your lease agreement• BRRRR Method 101: Tips for Success in Long-Term Rentals with Jessie LangThanks to everyone who submitted questions. To hear your voice on the show and send a question to Sarah and Annette, submit your burning hosting questions at: hostinghotline.com.Resources:• Furnished Finder: furnishedfinder.com• Youtube: Parent Child Listing• Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned in this episode:Hosting Handbook | Get everything you need to fast track your way to Superhost at thanksforvisiting.com/handbookStayFi | 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!

Today’s expert guest is Keith Brady. Owner of Florida Vacation Rental Law, he’s Florida's leading authority on vacation rentals. Keith has dedicated his career to the vacation rental industry and offers counsel to governments, businesses, and individuals.Keith’s here to give us the cold hard facts about vacation rental chargebacks. The truth is, you’re very likely to be at risk! More truths? Chargebacks are a scam. They make us feel powerless. They force us to question the good in the world. They make us mad! But – they can also be avoided. And we even have a few useful steps to take after experiencing a vacation rental chargeback.Keith walks us through several useful steps to take in our messaging which drastically reduce our susceptibility to fraudulent chargebacks before, during, and after a contested reservation takes place. He’s an open book in sharing secrets of the trade, detailing his own professional experience, and leaving us with actionable steps to help protect against scammers.Don’t leave your business open to be taken advantage of! Preventative care is the name of the game. Huge thanks to Keith for sharing this important information with the Thanks For Visiting audience.(00:01:24) #STRShare: @seascapevillastx(00:03:24) Introducing Keith Brady: Vacation Rental Law Expert(00:11:49) Tried & True Methods to Circumvent STR Credit Card Fraud(00:19:20) How to Avoid Short-Term Rental Chargebacks (00:33:36) Tips to Combat Fraudulent STR Chargebacks(00:40:19) What to Do AFTER Losing/Winning an STR Chargeback CaseResources:• Click here for full show notes• Website: floridavacationrentallaw.com • Email: [email protected]#STRShareSunday: @seascapevillastx• Submit your property for our next #STRShare at STRShare.com• Video: 7 Creeping .. Airbnb Business Expenses 😬 Look Out! • Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned 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!Superhog | Visit superhog.com/thanks-for-visiting and book your FREE demo today!Hosting Handbook | Get everything you need to fast track your way to Superhost at thanksforvisiting.com/handbook

Welcome back to the Hosting Hotline! This is an Ask Me Anything where each week we’ll answer your questions on Airbnb, STRs, real estate, and everything in between.John asks:I'm in a ton of Facebook groups, and the most common question I'm seeing is… Should I charge for this or that? It could be a stained towel, a broken plate, a mark on a chair, all the way to wall damage or broken tiles. There are just so many opinions; I'd rather hear from the experts. What's the cost of doing business and what's not? How do you decide? (00:01:40) John Asks About the Cost of Doing Business as an Airbnb Host(00:04:02) Setting an Effective Threshold for STR Guest Damage Claims(00:06:20) Setting Up a Vacation Rental Damage Waiver Program(00:08:03) Pros & Cons to STR Damage Claims: Marketing, Time Investment & CommunicationThanks to everyone who submitted questions. To hear your voice on the show and send a question to Sarah and Annette, submit your burning hosting questions at: hostinghotline.com.Resources:• Click here for full show notes• Check out Relay: lets.bankwithrelay.com/thanks-for-visiting • Check out Superhog: superhog.com/thanks-for-visiting • Video: 10 Must Have Apps for Airbnbs & Short Term Rentals• Airbnb Essentials Checklist: hostchecklist.comThanks for Visiting is produced by Crate Media.Mentioned in this episode:Hosting Handbook | Get everything you need to fast track your way to Superhost at thanksforvisiting.com/handbookQuiz | Take our quiz to reveal your hosting personality style!