The Mid-Term Rental Show

Bailey Kramer
  • 5.0 (4)
  • INVESTING

The #1 podcast for active and aspiring Mid-Term Rental operators. Hosted by investor Bailey Kramer, this show breaks down how to find the best markets, analyze deals, furnish for profit, and consistently fill your units with high-quality guests. Get real strategies, real stories, and real results from an operator actively building his MTR portfolio. Learn what works, skip what doesn’t, and grow with confidence while you build long-term freedom through Mid-Term Rentals. Whether you manage one unit or fifty, you’ll get practical, step-by-step insights you can use right away.

  1. 4H AGO

    How To Manage Mid-Term Rentals Remotely (From South Korea!)

    In this episode of The Midterm Rental Show, I sit down with someone I have real history with — Alisha, who used to work with me in my co-hosting company years ago. Since then, she’s built and managed a remote portfolio while navigating military life, deployments, live-in renovations, two babies, and multiple cross-country moves. We talk about: How she transitioned from short-term rentals to midterm rentals Why Furnished Finder became her #1 booking source Her exact screening and leasing process (including the tools she uses) Why midterm rentals have been more stable and “chill” than short-term rentals How she runs everything remotely (including her Walmart starter pack system) Maintenance lessons from owning a 1905 home The real reason she’s building a new construction short-term rental How her builder structured the deal so she doesn’t carry the construction risk Her 5-year vision: 6–10 cash-flowing properties to fund travel after military retirement We also dive into: Using Avail for leases, payments, and background checks Hospitable, Turno, and PriceLabs Why reserves matter more than people think The military “nomad investing” strategy How lifestyle plays a huge role in investment decisions This episode is a real look at building wealth while juggling real life — deployments, young kids, relocations, and long-distance management. If you’re curious about: Midterm vs short-term rentals Investing near military bases Building remotely Or structuring a new construction STR deal You’re going to love this one.

    47 min

  2. 3D AGO

    The Airbnb market collapsed, here's what to do instead

    Host Bailey Kramer explains why short-term rentals have become much harder than they were 2–4 years ago and outlines five main causes: (1) supply has exploded since the COVID-era boom while travel demand has normalized, creating intense competition and a race to the bottom on price; (2) guests are booking last minute because they see abundant availability, which reduces revenue predictability and forces hosts to discount; (3) Airbnb’s fee shift to a 15.5% host fee (0% guest fee) makes listings feel more expensive to guests, contributing to more 4-star reviews and review-related risk; (4) increasing regulation and uncertainty as cities restrict or tax short-term rentals; and (5) rising guest expectations for expensive amenities (hot tubs, murals, game rooms, pickleball courts, etc.) that are costly to maintain and can drive refunds and lower reviews. Kramer recommends pivoting to midterm rentals (30+ night stays), which target different tenants such as traveling nurses, construction crews, corporate relocations, displaced families, and people between home purchases who prioritize safe, furnished housing with fast Wi‑Fi and a stocked kitchen over luxury amenities. He argues there is less competition for longer stays (e.g., 60-night searches show fewer listings), fewer turnovers, lower operational stress, and more predictable income. He shares that he shifted from short-term rentals to running 10 midterm rental units and gives an example of a property averaging $2,800/month that could gross around $3,000 as a short-term rental but with far more turnovers and operational burden. He notes that while peak revenue may be slightly lower, stability and reduced expenses can improve profitability, and that short-term rentals still work mainly for ultra-luxury or ultra-unique properties. He suggests struggling hosts try setting a 30-night minimum stay and invites viewers to learn more via his podcast, YouTube channel, or Instagram.00:00 Why Airbnb Feels Impossible Right Now (Intro + What You’ll Do Instead)01:10 Reason #1: Supply Explosion + Demand Normalized (Race to the Bottom)02:20 Reason #2: Last-Minute Bookings Kill Predictability03:32 Reason #3: Airbnb Fee Shift = Higher Prices, Lower Reviews04:39 Reason #4: Regulation Risk and City Crackdowns05:21 Reason #5: Sky-High Guest Expectations & Amenity Burnout06:16 The Pivot: Why Midterm Rentals Win (30–60+ Night Stays)06:56 Who Midterm Rentals Serve + How to Spot the Opportunity08:03 Real Portfolio Example: More Stability, Fewer Turnovers, Strong Margins09:30 Wrap-Up: Airbnb Isn’t Dead—Pivot to 30+ Nights + Next Steps

    11 min

  3. 5D AGO

    How my Fiance and I handle our Finances...

    In this episode of The Midterm Rental Show, I’m letting you in on a very personal conversation I had with my fiancée about money as we prepare to get married and combine finances. We’ve been together for nine years. We’ve lived together. We’re building a life together. And now we’re building a financial plan together. This episode breaks down: How we’re structuring our joint finances once we’re married Why I’m matching her salary into our joint account (even though I earn more) The strategy behind living on less than we technically “can” afford Why we’re intentionally avoiding lifestyle creep The quote that completely reshaped how I think about wealth “If you stay small enough, long enough, you’ll be big enough soon enough.” I explain how this philosophy applies to real estate, investing, marriage, and life. We walk through real numbers, including how compounding works, why reinvesting matters more than upgrading your apartment, and how building a large enough asset base can eventually fund an extraordinary life off a small percentage of returns. This is about discipline. Patience. Long-term thinking.And choosing future freedom over short-term flexing. If you’re building a business, investing in real estate, or navigating money conversations with a partner, this episode is for you. 🎧 Listen in and let me know your thoughts.DM me on Instagram if you agree, disagree, or are having similar conversations in your own relationship.

    10 min

  4. FEB 16

    Optimizing Your Midterm Rentals for Success: Key Insights from a Coaching Call

    🔗 RESOURCES & SOFTWARE MENTIONED: • Book a 1:1 Coaching Call with Me• Baselane (Free Banking + Bookkeeping – Affiliate Link) • Minoan (Free Furniture Discounts)• Amazon Business• Walmart Business PlusIn this episode of the Midterm Rental Show, host Bailey Kramer discusses critical takeaways from a recent coaching call with a midterm rental owner facing challenges with property bookings. Key topics include removing friction from Airbnb listings, updating property decor, optimizing minimum night stay settings, cost-saving strategies for Wi-Fi, efficient bookkeeping, and operational efficiencies like smart locks and business account benefits. Bailey shares actionable tips to improve midterm rental performance and highlights the importance of reinvesting in properties to sustain income flow. Listeners are encouraged to book one-on-one coaching sessions for personalized advice.00:00 Introduction and Episode Overview00:57 Identifying the Problem: Friction in Listings02:47 Improving Property Decor and Amenities03:28 Optimizing Minimum Night Stay Settings04:28 Cost-Saving Tips for WiFi and Utilities05:51 Streamlining Bookkeeping and Operations06:28 Tools for Operational Efficiency08:37 Final Advice and Conclusion

    10 min

  5. FEB 13

    How I’m Pulling $20,000 Out of One Property (Without Selling It)

    In this episode of The Mid-Term Rental Show, I break down exactly how I’m about to receive $20,000 in tax-free cash from a property I bought in 2022… without selling it. This isn’t clickbait.This isn’t some risky creative financing trick.This is simply understanding how to use equity the right way. Back in 2022, I bought a property for $115,000 at an 8.5% interest rate — when everyone else was scared to buy. I had never seen the property in person. I had never even been to the city. Fast forward to today: The property is now worth around $150,000 My loan balance is roughly $78,000 I’m refinancing it into a new loan I’m pulling out about $20,000 My payment stays roughly the same My interest rate drops And the $20,000 I receive is not taxed In this episode, I walk you through: Why buying when others are fearful can create massive opportunity How appreciation and leverage actually work in real life A simple breakdown of a cash-out refinance Why refinance money is not considered taxable income How this strategy can be repeated over and over Why real estate gives you options that most assets don’t This is one of the core reasons I love Mid-Term Rentals. Not just for cash flow. Not just for tax benefits. But for the long-term equity plays that allow you to recycle capital and scale. If you’re serious about building a portfolio that pays you today and funds your future growth, this episode is a must-listen. As always, if you got value from this episode, share it with someone who needs to hear it. See you in the next episode.

    7 min

  6. FEB 11

    Legal Win + Pipe Burst: A Real Day in My Mid-Term Rental Business

    In this episode of The Mid-Term Rental Show, I’m pulling back the curtain on a very real day inside my mid-term rental business—the good, the stressful, and everything in between. First, I break down a legal situation with a traveling nurse tenant who attempted to leave early without honoring the lease. I explain how I handled the situation, the role the lease played, and how it ultimately resulted in a signed early termination agreement and a clean resolution—without going to court. Then, on the complete opposite end of the spectrum, I walk through a same-day emergency where a pipe burst behind a wall, flooding part of a property during a short-term gap stay. I share how I responded, coordinated repairs, communicated with guests, and leveraged insurance to cap my downside. This episode is all about staying calm, knowing your systems, and understanding risk as a mid-term rental operator—because things will go wrong, and that’s part of the business. How to handle early move-outs when a tenant refuses to cooperate Why strong lease language matters (and how it protects you) How to respond quickly and calmly to property emergencies When to involve insurance—and how to think about deductibles Why mindset matters just as much as systems in this business If you’re building or scaling a mid-term rental portfolio and want a transparent look at what ownership really looks like, this one’s for you. 🎧 Tune in and let’s get into it. What you’ll learn in this episode:

    8 min

  7. FEB 9

    5 Raw Truths About Buying Your First Mid-Term Rental

    Buying your first mid-term rental is exciting — but let’s be honest, it’s also uncomfortable, intimidating, and full of unknowns. In this episode of The Mid-Term Rental Show, Bailey breaks down five raw truths every investor needs to hear before buying their first mid-term rental. These aren’t the polished, Instagram-friendly talking points — these are the real lessons that determine whether someone takes action or stays stuck on the sidelines. If you’ve been overanalyzing deals, waiting for interest rates to drop, or second-guessing yourself, this episode is for you. • Why your first deal is always the hardest (and why that’s normal)• Why your first mid-term rental does NOT need to be a home run• How your first deal acts as a proof of concept and confidence builder• Why interest rates matter far less than most people think• What “date the rate, marry the house” actually means in real life• Why people will doubt you — and how that can quietly stop you from investing Bailey also shares personal stories from buying his first mid-term rental at peak interest rates, ignoring outside noise, and using that first deal as the foundation to build a multi-unit portfolio. Your first mid-term rental isn’t about perfection. It’s about momentum. Once you prove to yourself that you can do it once, everything else becomes easier. Bailey currently offers two ways to work together:• 1-on-1 coaching where you learn the process step by step• A Done-For-You Mid-Term Rental option that’s fully hands-off To qualify, you’ll need at least $50,000 saved and a 680+ credit score. If this episode resonated with you, send Bailey a message on Instagram and let him know you listened. What you’ll learn in this episode:Key takeaway:Want help buying your first mid-term rental?

    9 min

  8. FEB 7

    Is Now a Good Time to Get Into Mid-Term Rentals?

    Is now actually a good time to get into mid-term rentals? Or should you wait for interest rates to drop, prices to fall, or the “perfect” market conditions? In this episode of The Mid-Term Rental Show, Bailey breaks down why this question almost always comes from beginners and why focusing on timing the market is one of the biggest mistakes new investors make. Using real data from one of his own mid-term rental markets, Bailey walks through how supply cycles actually work, why competition naturally rises and falls, and how investors who stay the course are rewarded when others panic and exit. If you’ve been sitting on the sidelines waiting for the “right time,” this episode will reframe how you think about real estate investing entirely. • Why “time in the market” matters more than timing the market• How Airbnb and furnished rental supply naturally cycles up and down• What happens when too many investors flood a market too quickly• Why many investors quit during short downturns (and why that creates opportunity)• How Bailey bought his first mid-term rental when rates were high and people were scared• Why a long-term mindset is non-negotiable for real estate success• When it isn’t a good time to invest in real estate Bailey also explains how holding through slower periods allowed him to raise prices later, benefit from appreciation, and stay positioned for long-term cash flow and flexibility. If you’re willing to hold for at least five years and operate with a long-term mindset, it’s always a good time to get into real estate. The worst strategy is waiting on the sidelines trying to predict the perfect moment.

    9 min
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About

The #1 podcast for active and aspiring Mid-Term Rental operators. Hosted by investor Bailey Kramer, this show breaks down how to find the best markets, analyze deals, furnish for profit, and consistently fill your units with high-quality guests. Get real strategies, real stories, and real results from an operator actively building his MTR portfolio. Learn what works, skip what doesn’t, and grow with confidence while you build long-term freedom through Mid-Term Rentals. Whether you manage one unit or fifty, you’ll get practical, step-by-step insights you can use right away.

Information

  • Creator
    Bailey Kramer
  • Years Active
    2025 - 2026
  • Episodes
    52
  • Rating
    Clean
  • Copyright
    © Bailey Kramer
  • Show Website
    The Mid-Term Rental Show

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