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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

Interested in a FREE 1 on 1 coaching call (will be recorded for the podcast): Click HereBailey 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

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Bailey Kramer hosts the Midterm Rental Show and explains five common mistakes people make when trying to start midterm rentals: underestimating how many offers, negotiations, and follow-ups it takes to land a good deal; wanting absolute certainty on income despite real estate having no guarantees; spending too much time learning and not enough time taking action (choosing a market, underwriting deals, submitting offers); moving too slowly and missing great deals because they can’t decide fast enough; and expecting the first deal to be perfect instead of using it for experience and proof of concept, noting even a lower cash-on-cash return can still compare favorably to typical stock market returns and provide monthly cash flow. He also mentions his Done For You Midterm Rental service to help clients find markets and properties and get set up, emphasizing real estate moves fast.00:00 Welcome and Overview00:37 Mistake One Offer Volume02:52 Mistake Two No Guarantees05:37 Mistake Three Take Action08:11 Mistake Four Decide Faster11:29 Mistake Five Not Perfect15:13 Wrap Up and Next Steps

Bailey Kramer, a full-time real estate investor and longtime Hospitable user, joins the Hospitable Host podcast to explain his shift from co-hosting up to 30 short-term rentals across multiple markets to primarily owning and operating 10 midterm rental units. He says the main driver was operational burden from frequent STR turnovers, while MTRs run at a slower pace with fewer turnovers and can be managed solo using similar systems. Kramer addresses misconceptions that MTRs are less profitable, noting STR revenue can be higher but often carries heavy turnover-related costs; he highlights utilities as an overlooked MTR expense. He discusses using Hospitable for automated messaging, cleaner coordination, smart lock codes, and managing manual bookings from Furnish Finder and insurance stays, and emphasizes minimum-night settings and a hybrid STR/MTR seasonal approach. He also shares why he launched the Midterm Rental Show and a community to cover MTR-specific nuances, stressing patience and long-term mindset.00:00 Welcome and Episode Setup00:53 Meet Bailey Kramer01:45 From Co Hosting to Ownership02:22 Why Switch to Midterm Rentals03:46 Midterm Profit Misconceptions05:00 Operations at Slower Speed06:28 Using Hospitable for MTRs07:52 Systems That Break First09:16 Hybrid STR to MTR Strategy10:58 Podcast and Community Launch13:50 Scaling Mindset and Patience16:47 Quick Fire Midterm Q and A19:22 Where to Find Bailey20:18 Wrap Up and Subscribe

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Bailey Kramer shares three rules of thumb for finding strong midterm rental deals: (1) the “2% rule,” targeting average monthly rent around 2% of the purchase price (with higher percentages being better), (2) focusing on deal structure—not just price—by using tactics like seller credits, financing small price increases to reduce cash to close, and buying furnished to improve cash-on-cash returns, and (3) recognizing that great deals require time, volume, negotiation, and follow-up, including making many offers. He also describes his done-for-you midterm rental service that helps clients choose markets, analyze and underwrite all qualifying listings, and negotiate terms to turn good deals into great ones, typically working with investors who have at least $50,000 saved and a 680+ credit score.00:00 Welcome and Overview00:47 Key One 2% Rule02:18 Key Two Deal Structure05:51 Key Three Do the Work07:10 Done for You Service07:43 How We Find Deals09:37 Who We Work With10:06 Wrap Up and Next Steps

Bailey Kramer shares a transparent personal and business update, including wins and regrets. He is pursuing a cash-out refinance on his first solo rental property bought for $115,000 at 8.5% interest, expecting to lower the rate to about 6.5%, pull out roughly $30,000, and keep the payment increase under $100, with plans to refinance another property next. On the downside, he is selling his Tesla Model 3, which he bought to reduce a large tax bill but now regrets due to high monthly costs and being upside down (owing about $30,000 on a $22,000–$25,000 value). He also regrets financing 50% of his fiancée Ellie’s engagement ring, now paid off. He shares that his South Africa/Mauritius honeymoon is booked largely using points, his done-for-you midterm rental service is growing with many experienced investors, he outlines a vision to partner on real-estate-related companies, notes podcast download growth, invites guests, and plans review incentives.00:00 Welcome and Format01:05 Cash Out Refi Win04:09 Tesla Debt Regret10:09 Honeymoon Plans11:18 Ring Financing Lesson13:56 Done For You Growth16:38 Big Vision and Hiring20:59 Podcast Community Push23:40 Wrap Up and Thanks

Bailey Kramer explains his approach to making offers in today’s market by focusing on numbers that work for him rather than list price. He recounts buying a property listed at $110,000 by initially offering about $60,000 and ultimately closing at $85,000, which has since performed well as a midterm rental. He then describes calling an agent about another nearby listing (3 bed/1 bath, 884 sq ft) priced at about $170 per square foot despite needing roughly $20,000 in repairs, and suggesting an offer around $75,000 based on $85 per square foot; the agent laughed and noted the sellers don’t want an investor. Bailey notes the home has been on market 45 days, the seller moved in with a fiancé, and emphasizes that time can increase seller motivation, so investors should submit low offers and follow up.00:00 Welcome and Topic00:13 Recent Offer Context00:39 Last Deal Lowball Win01:53 New Listing Breakdown02:50 Calling the Listing Agent03:47 The Lowball Math05:06 Seller Motivation Intel05:37 Why Time Creates Leverage06:23 More Lowball Examples06:51 Final Takeaways

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Bailey Kramer explains which property types work best for midterm rentals by comparing one-bed/one-bath units, two-bed/one-bath houses, three-bed/one-bath houses, and three-bed/two-bath houses using examples from his portfolio. One-bed units primarily attract traveling healthcare professionals (typical 13-week stays, often extending) and are cheap to furnish but have a limited renter pool; his $150,000 triplex units rent for $1,650/month. Two-bed/one-bath homes draw a mix of insurance stays, traveling nurses, construction workers, and pet owners, averaging $2,500/month but face heavier competition. Three-bed/one-bath homes rent around $3,000/month and host more people but have higher utilities and a one-bath limitation. Three-bed/two-bath homes offer the most flexibility, lower competition in his market, rent about $3,000–$3,500/month, and are his top pick.00:00 Best Property Question00:35 Portfolio And Game Plan01:04 One Bed One Bath03:18 Two Bed One Bath05:30 Three Bed One Bath07:01 Three Bed Two Bath08:18 Key Takeaways08:50 Final Pick And Wrap

In this video, I compare three rental strategies:

• Long-Term Rentals

• Short-Term Rentals

• Midterm Rentals

I grade each one across five key categories:

• Cashflow
• Stability
• Scalability
• Management Intensity
• Barrier to Entry

Each strategy gets scored out of 50.

Some results might surprise you.

One strategy is incredibly stable but lacks upside.
One can produce strong income but demands serious time and effort.
And one hits a balance that most investors overlook.

If you're trying to figure out which model actually fits your goals — this breakdown will help you think about it differently.

00:00 Ranking Rental Strategies

00:29 Long Term Rentals Explained

00:58 Long Term Score Breakdown

03:52 Short Term Cashflow Reality

05:04 Short Term Scalability and Workload

07:30 Midterm Rentals Overview

08:02 Midterm Scores and Scalability

09:55 Midterm Barrier Mindset

11:46 Final Rankings and Wrap Up

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.