Advertise on podcast: The Mid-Term Rental Show

🎁 Want to buy your first mid-term rental? Grab my FREE Mid-Term Rental Beginner's Guide here: https://stan.store/baileykramer/MTRbeginnersguidepodcast Winter is coming. And depending on how you approach it, that could be a problem… or a HUGE opportunity. After years of owning and operating mid-term rentals across multiple markets, I've learned that winter is a completely different ballgame. Properties sit vacant. Competition changes. Owners panic. But here's the thing: Some of my best real estate moves have happened during this time of year. In this episode of The Mid-Term Rental Show, I'm breaking down what you should be doing right now, whether you already own mid-term rentals, you're running an Airbnb, or you're looking to buy your very first investment property. Here's what we're getting into: Current MTR owners: How to adjust your pricing, monitor your competition, and fill vacancies during slower months. Airbnb owners: Why switching to mid-term rentals during the winter could make you more money (and why those holiday bookings might actually be hurting you). Future investors: Why Q4 is one of my favorite times to buy rental properties and how to take advantage of a slower housing market. Everyone: Why you shouldn't panic over a few slow months and how to think about real estate for the long haul. I'll also share what I'm seeing across my own rental portfolio heading into winter and the adjustments I'm personally making. Bottom line: Winter doesn't have to be the season your rental business struggles. It might actually be where you find your next big opportunity. — Bailey KramerHost, The Mid-Term Rental Show

Want to buy your first mid-term rental? Grab my FREE MTR Beginner's Guide:https://stan.store/baileykramer/MTRbeginnersguidepodcast Buying your first rental property can feel OVERWHELMING. How much money do you actually need? What if you buy a bad property? What happens if you can't find tenants? And how the hell are you supposed to know what you're doing if you've never done it before? 😂 In this episode, I'm breaking down 8 things I wish I knew before buying my first mid-term rental. We're talking about: Why your first rental property probably WON'T make you rich (and why that's okay). How much money you actually need to buy your first property. Why inspection reports aren't nearly as terrifying as they look. The hidden loan fees that could cost you THOUSANDS. Why I NEVER buy a property that only works as a mid-term rental. And a few other lessons I learned along the way. Whether you're actively looking for your first property or you're still trying to figure out where to start, this is the advice I'd give my younger self. Hope you enjoy the episode! — Bailey

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: https://stan.store/baileykramer/MTRbeginnersguidepodcast A lot has happened since my last episode. I got married, honeymooned in South Africa, lost 20 pounds, and moved from Denver to Milwaukee. And while I stepped away from posting, my mid-term rentals kept going. In this episode, I’m catching you up on life and business—including my fully occupied 10-unit portfolio, how my properties ran while I was on my honeymoon, and a four-unit deal I’m chasing that just came back on the market. I’m also sharing what’s next for The Mid-Term Rental Show, what I’ve learned about burnout, and why I’m getting more focused on helping people buy their first mid-term rental. If you’ve been here a while, thanks for sticking around. If you’re new, welcome. I’m excited to be back!

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast⁠ Furnishing a mid-term rental doesn't have to be expensive, overwhelming, or a logistical nightmare—especially when you're managing the entire setup remotely. In this episode, I'm breaking down the exact tools, websites, and strategies I'm using to furnish a client's property in Florida, taking it from completely vacant to fully furnished and ready for guests. I'll share how we organize every furniture order using Google Sheets, where we're finding the best deals, and how we're coordinating deliveries from multiple retailers to arrive on the same day. You'll learn how we're saving $800 at Costco, getting additional discounts through Amazon Business and Minoan, and using a simple FedEx and UPS trick to avoid packages piling up outside the property. I'll also walk through our upcoming Florida installation schedule, from furniture assembly to professional photos and handing the keys back to the owner. TIMESTAMPS 00:00 Introduction 00:18 Furnishing a Client's Florida Property 01:18 Organizing Everything with Google Sheets 02:43 Costco Furniture Deals and $800 in Savings 04:05 Amazon Business Discounts and Delivery Scheduling 05:45 Minoan Discounts for Wayfair and Crate & Barrel 06:50 Walmart Business Plus and Sam's Club 07:26 Coordinating Deliveries with FedEx and UPS 08:36 Our Florida Furniture Installation Schedule 09:28 Property Handoff and Co-Hosting Options 10:18 Final Thoughts and Behind-the-Scenes Content

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Host Bailey Kramer shares 18 personal facts that may surprise people despite his owning over $1M in real estate: he owns no stocks or crypto (though his fiancée does), rents instead of owning a home, doesn't own or lease a car, and has no personal debt. He's frugal with clothing and possessions, keeps an older iPhone by replacing the battery, and uses credit card points (especially Southwest Companion Pass) to make most flights nearly free. His biggest recurring expenses are health-related (gym, recovery studio, workout app, meal prep). He makes decisions quickly, prioritizes travel experiences over five-star hotels, and rarely talks real estate with friends/family. He's the first in his family to own rentals, dropped out of college in his last semester as his co-hosting business grew, started working in high school, learned money habits largely by doing the opposite of his parents, struggles with hiring/delegating, and becomes introverted in groups of five or more. 00:00 18 Surprising Money Habits00:17 No Stocks Just Real Estate01:30 Why I Still Rent02:48 Living Without a Car04:48 Zero Personal Debt05:28 Cheap Clothes Simple Style07:02 Not Into Flashy Stuff08:18 Keeping the Same iPhone09:47 Free Flights With Points11:29 Spending on Health13:45 Fast Decisions Minimal Thinking15:07 Experiences Over Luxury Hotels16:56 Real Estate Stays Offline17:47 No Family Rental Background18:52 Dropping Out to Build Business23:29 Working Since High School27:08 Money Lessons From Parents28:56 Hiring and Delegation Struggles29:43 Introvert in Big Groups30:42 Wrap Up and Takeaways

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Bailey Kramer thanks listeners for their feedback and shares that he is hiring a virtual assistant to take over low-dollar, time-consuming tasks like guest and tenant messaging so he can focus on higher-value work. He recounts dropping out of college after earning $5,000/month from a co-hosting business, scaling to 30 managed properties, then reducing to about 10 to focus on acquiring his own portfolio, now at 10 units, with another potential deal pending. He plans to grow his co-hosting business in Q2–Q3 2026, especially for midterm rentals, leveraging insurance and travel-nurse connections plus operational systems and preventative maintenance, and invites owners to reach out. He will document the VA hiring/training process and is also hiring full-time content help. He closes with a health update: after a DEXA scan showed 25% body fat, he's cutting calories, training five days/week, and aiming toward 15%. 00:00 Welcome And Thanks01:02 Why Hire A Virtual Assistant01:15 Dropping Out And Early Hustle02:40 Scaling Co Hosting Then Buying03:17 Cutting Clients And Refocusing05:05 Delegating Low Value Tasks06:53 Growth Plan For 202608:41 Offer Co Hosting Help09:09 Documenting VA And Content Team10:53 Health Journey Segment11:24 DEXA Results And Goals12:34 Training Diet And Progress13:48 Wrap Up And Contact

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Host Bailey Kramer shares a done-for-you midterm rental client deal for Stehon: a Midwest duplex found on Redfin with only exterior photos, listed at $115,000 and now under contract for $95,000. The fully occupied property currently brings in $1,500/month total on month-to-month leases, with a plan to renovate and furnish each unit into midterm rentals expected to generate about $3,000/month combined. Investor First Capital is providing a hard money loan, with Stephon bringing roughly $15,000 to closing. Units will be renovated one at a time while managing tenant move-outs to maintain some income, then refinanced with an estimated after-repair value around $150,000 to reduce out-of-pocket cash. Bailey also mentions another client fourplex opportunity and a possible Florida trip to document furnishing a new-build midterm rental. 00:00 Show Intro00:15 Done For You Service00:41 Finding The Duplex01:40 Negotiation And Walkthrough02:33 Under Contract Numbers03:13 Renovation And Refi Plan05:13 More Deal Examples06:10 Upcoming Florida Setup06:44 Questions And How To Reach Me07:30 Wrap Up And Next Videos

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠⁠⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Host Bailey Kramer shares a portfolio update on the Midterm Rental Show, outlining his busiest midterm rental week in months with five of his 10 units turning over. He details each checkout: a one-month traveling medical student with a near-immediate replacement; a 243-night insurance-claims stay ending April 1 with no replacement after a Furnish Finder lead fell through; a three-month guest leaving with a future tenant already leased and paid via Baselane starting in June (leaving April–May to fill); a construction worker checking out with a new six-month stay lined up about a week later; and a three-to-four-month guest with a next-day move-in. Overall, three units have immediate move-ins and two need filling, highlighting that occupancy and turnover timing can vary widely. 00:00 Big Week Preview00:15 Why Five Checkouts00:54 Checkout One Quick Turn01:21 Long Insurance Stay Ends02:07 Gap Until June Lease02:35 Construction Worker Swap02:58 Three Move Ins Two Vacancies03:26 Transparency And Next Steps03:59 Midterm Reality Check04:23 Wrap Up And Sign Off

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠⁠⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Host Bailey Kramer recounts a problematic midterm Airbnb stay that began with a January six-month inquiry from a local employee booking for a European coworker. After refusing a pre-booking tour, Bailey allowed a post-booking walkthrough with his cleaner, and the local booker later did another walkthrough before move-in, both finding the home fine. Once the European guest arrived, she reported a kitchen window leak and then sent multiple nitpicky cleaning photos, demanded a deep clean, and was described by the cleaner as extremely OCD (e.g., checking behind the fridge). Weeks later, the local employee reported nonstop complaints and threats to report the listing; she arranged another inspection with Bailey's handyman and cleaner, which triggered the guest's camera alerts and demand that the cleaner leave. The inspection found only minor fixable issues, and the company decided to move the guest to an extended-stay hotel, shortening the reservation to one more month. 00:00 Welcome and Setup00:17 January Booking Inquiry01:55 Pre Booking Walkthrough Rules03:06 Move In Day Issues Begin04:48 Cleaning Complaints and Deep Clean07:44 Three Weeks Later Escalation Call10:47 Inspection and Camera Drama12:38 Decision to End Stay Early13:38 Lessons Learned and Wrap Up

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠⁠⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Bailey Kramer hosts an episode of the Midterm Rental Show on furnishing midterm rentals completely remotely, sharing a process he's used for 4–5 years and is currently applying for a Florida new-build client while he's in Colorado. He notes he's hiring help for podcast/YouTube editing, then explains that having a full floor plan with dimensions makes remote furnishing much easier, followed by aligning on the client's vision and building a room-by-room mood board. He uses a customizable furnishing and supplies checklist template and sources most furniture from Wayfair (often with Minoan discounts), plus Costco for select items like a couch and dining set, Amazon for kitchen/bath essentials (via a business account), and sometimes Walmart depending on property price point. For design mockups, he uses ChatGPT image generation, and for assembly he hires local help via Thumbtack, coordinating with photos and FaceTime. 00:00 Welcome to the Show00:22 Housekeeping Updates01:02 Why Remote Furnishing Works02:27 Floor Plans and Vision03:42 Furnishing Checklist Template04:36 Where to Buy Everything07:33 Using ChatGPT for Mockups08:44 Local Install and Assembly09:35 Wrap Up and Next Steps

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠⁠⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Bailey Kramer shares completing a cash-out refinance on her first solo midterm rental, bought in 2022 for $115,000 (listed at $130,000) with an 8.5% rate and about $35,000 down. The property has averaged $2,500–$3,000 per month and appreciated; a recent appraisal came in at $145,000. He refinanced into a new $108,000 loan at 6.6%, paid off the prior $80,000 mortgage, and received a $19,734.94 tax-free wire after lender fees (~$2,700) and required prepaid insurance and taxes, with an additional escrow refund expected. Despite the larger loan balance, the lower rate keeps payments about the same. He explains cash-out refinancing, plans to reinvest the proceeds into future real estate opportunities, and is delaying a similar refinance on her triplex until rates drop back into the sixes. TIMESTAMPS 00:00 Cash Out Refi Reveal00:47 Backstory First Rental02:12 Property Performance Wins02:36 Why Refinance Now03:23 Cash Out Refi Explained05:03 Fees Closing Breakdown06:45 Rates Next Refi Plan08:00 Reinvesting The Proceeds08:39 The Real Estate Cheat Code09:35 Wrap Up And Next Steps

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠⁠⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Bailey Kramer shares the most common feedback he gives midterm rental hosts whose listings aren't getting booked, based on a recent paid listing review. He emphasizes pricing based on current market alternatives and competition rather than past performance, and recommends using professional, photo-ready staging and photography. He advises making a phone number accessible on Furnish Finder (using a business number if needed) and adding a host profile photo on Airbnb, noting that missing photos and zero reviews reduce trust. He strongly suggests allowing pets to stand out since fewer listings do, and charging a premium if desired. For new listings, he recommends finding ways to get initial reviews, and ensuring Airbnb amenities are accurately checked so the property appears in guest filters. 00:00 Welcome and Episode Goal00:15 Why Listings Struggle01:19 Fix Pricing With Comps02:26 Upgrade Your Photos03:06 Add Easy Contact Options03:46 Build Trust on Airbnb04:18 Allow Pets for Demand05:14 Get Early Reviews Fast05:46 Complete Amenities Checklist06:20 Wrap Up and Next Steps

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠⁠⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Bailey shares a rapid update on personal and business events from the past week. He sold his Tesla to CarMax for about $25,000 while owing roughly $30,000, paying $5,000 to exit the loan and eliminating about $1,500/month in car-related expenses. A co-hosted Illinois duplex had a downstairs guest altercation involving police, an arrest, a hospital visit, guest removals, minor damages (broken windows, picture frame, pulled socket, floor vent, bloodstains), and vacancy while re-renting. Another Illinois co-host listing received a first booking: a 21-day July stay for about $18,000. He found a duplex deal for a client (listed $115,000, negotiated to around $90,000) and a furnished $350,000 fourplex. He joined a cold plunge/sauna facility, is pursuing cash-out refinances, submitted two lowball offers, completed a Baselane-sponsored YouTube video, and had a virtual assistant quit. 00:00 Weekly Updates Intro00:53 Selling the Tesla04:29 Duplex Guest Altercation06:53 Big First Lake Booking07:54 Client Deal Finds09:30 Cold Plunge Wellness11:04 Cash Out Refi Plans11:41 Lowball Offers Strategy12:33 Baselane Sponsorship13:54 VA Quits and Lessons15:42 Wrap Up and Thanks

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠⁠⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Bailey Kramer explains why out-of-state real estate investing is a major opportunity and argues that being far from a property shouldn't prevent investors from getting started, especially if their local market numbers don't work. He says many people overestimate the value of personally visiting properties and confuse emotional comfort with effectiveness, since most problems still require hired experts. Kramer notes that being local can create unproductive habits of handling low-value tasks, and emphasizes that remote success depends mainly on having a strong cleaner and handyman, supported by systems like smart locks, photos/videos from vendors, and online tools for rent collection, automation, and screening. He shares his experience running properties remotely (including 30 short-term rentals) and says midterm rentals are operationally easier, adding he rarely visits except sometimes to furnish a property to save money. 00:00 Out of State Mindset03:12 Why Proximity Feels Safe04:54 Tangible Doesn't Mean Touch06:08 What If Something Breaks08:02 Local Can Hurt Scale09:12 Cleaner and Handyman Duo10:13 Starter Kit Plug11:02 Systems and Smart Locks12:18 Midterm Easier Than STR13:15 You Don't Need Expertise15:22 When I Visit In Person16:07 Final Takeaways

Looking to buy your 1st Mid Term Rental? Grab my FREE MTR Beginners Guide: ⁠⁠⁠https://stan.store/baileykramer/MTRbeginnersguidepodcast Bailey Kramer explains why many investors misunderstand midterm rental market saturation by judging a city based on total listing counts rather than true comparable competition. He argues saturation is usually specific to bedroom count and property type, since different bedroom counts serve different guest avatars, budgets, and use cases. His key measure is how many similar options an ideal guest would realistically consider, because too many direct comparables reduces pricing power and squeezes margins. He recommends identifying the most common bedroom count to avoid, finding underserved bedroom counts, and then validating demand drivers such as hospitals, construction, universities, insurance placements, and major employers. He also stresses the numbers must still pencil on acquisition and returns, and that struggling hosts should objectively assess positioning (furniture, photos, layout, target guest) before blaming the market. 00:00 Market Saturation Myth01:14 Bedroom Count Lens02:24 Comparable Options Rule05:04 Supply Gap Checklist07:52 Demand Drivers Matter09:59 Free Coaching Invite11:06 Pricing Power and Numbers12:57 Positioning in Competition13:38 Key Takeaways and Wrap