The Mid-Term Rental Show

AI has completely changed the way I'm running my mid-term rental business, and I'm not talking about using ChatGPT to write guest messages.

I'm talking about using AI to monitor competitors, optimize pricing, follow up with leads, create lease agreements, track expenses, and automate tasks that used to take hours of my time.

In this episode of The Mid-Term Rental Show, I'm pulling back the curtain on how I've been using Claude AI to manage my portfolio of 10 mid-term rentals.

I'll break down some of the actual systems I've built, including:

• How AI monitors my competitors and helps me make smarter pricing decisions

• How I'm automating guest communication, lead follow-ups, and lease creation

• How AI helps catch missed bills and unexpected expenses

• How I've replaced certain paid software tools with custom AI workflows

• How you can start implementing similar systems in your own rental business

The crazy part? Many of these things can be done with an AI subscription that costs around $20/month.

Whether you own one rental or you're managing an entire portfolio, I think this episode will completely change how you think about using AI in your business.

Want to see these systems in action? I'm considering putting together a live masterclass where I walk through exactly how I've built and implemented these AI workflows. Send me a DM on Instagram @the_bailey_kramer if that's something you'd be interested in!

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]

Want help buying your first mid-term rental?

I'm currently accepting applications to work with one investor one-on-one to help them find, finance, renovate, and launch their first BRRRR + mid-term rental property.

Apply here: https://stan.store/baileykramer/p/apply-to-work-with-bailey-1-on-1-

What if you could buy a rental property, build equity, refinance to recover most (or even all) of your invested capital, AND generate strong monthly cash flow?

That's exactly why I love combining the BRRRR strategy with mid-term rentals.

In this episode of The Mid-Term Rental Show, I'm breaking down what I believe is one of the most powerful real estate investing strategies available today: BRRRR + MTR.

I'm sharing the actual mechanics, financing options, biggest risks, and lessons I've learned from building my own portfolio of 10 mid-term rental units.

We'll cover:

• What BRRRR (Buy, Rehab, Rent, Refinance, Repeat) actually means

• How to use hard money, private money, and traditional financing to fund deals

• How refinancing allows you to recycle your capital into additional properties

• A real deal where I purchased a property for $85K, invested roughly $25K in renovations, and had it appraised for $162K

• Why combining BRRRR with mid-term rentals can dramatically increase your cash-on-cash returns

• The biggest mistakes and risks investors need to understand

• Six practical tips I've learned from executing this strategy myself

• Whether BRRRR + MTR still makes sense in 2026 and 2027

This isn't a get-rich-quick strategy, and it's definitely not risk-free. But when executed correctly, BRRRR can help you build equity and recycle capital, while mid-term rentals can generate substantial monthly cash flow.

And in my opinion, that's a pretty powerful combination.

Subscribe to The Mid-Term Rental Show for real-world investing strategies, deal breakdowns, and honest lessons from building a cash-flowing rental portfolio.

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]

I'm trying something completely different on The Mid-Term Rental Show.

Welcome to the first (and potentially last) episode of Beyond Mid-Term Rentals, where I'm stepping away from the usual real estate conversations to share what's actually going on in my life.

No scripts. No pretending I have everything figured out. Just an honest conversation about my personal life, money, business, and the things I'm working toward.

In this episode, I'm opening up about:

• Losing 20–25 pounds: The DEXA scan that completely changed my perspective on my health, the challenges of tracking my food, and what I've learned along the way.

• Why I love money: From flying Emirates business class on my honeymoon to spending $128 on Lululemon pants, and why certain luxuries have changed how I think about making money.

• Creating experiences for others: My dream of treating friends, family, and even podcast listeners to unforgettable experiences.

• A health, wealth & friendship retreat: Why I'd love to bring ambitious people together for a weekend focused on getting healthier, building wealth, and making genuine connections.

• My dream content career: From documenting real estate projects to furnishing an entire mid-term rental in 24 hours.

• My $50K/month cash flow goal: Where I want to take my rental portfolio and why I'm exploring boutique hotels, multifamily, and other real estate opportunities.

• My biggest business dilemma: Should I build a coaching business, pursue podcast sponsorships, raise money to acquire properties, or do something completely different?

At 26, I've been fortunate enough to build a real estate portfolio that gives me financial freedom. But I'm realizing that figuring out what I actually want to do with that freedom is an entirely different challenge.

This episode is exclusively for podcast listeners. I'm not publishing it on YouTube or clipping it for Instagram.

I have no idea whether Beyond Mid-Term Rentals will become a weekly, monthly, or one-time thing. That's entirely dependent on your feedback.

If you enjoyed this episode (or hated it), I'd genuinely love to hear from you.

Send me a DM on Instagram: @the_bailey_kramer

Thanks for listening!

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]

🎁 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 Kramer
Host, The Mid-Term Rental Show

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]

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

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]

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!

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]

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

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]

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 Habits
00:17 No Stocks Just Real Estate
01:30 Why I Still Rent
02:48 Living Without a Car
04:48 Zero Personal Debt
05:28 Cheap Clothes Simple Style
07:02 Not Into Flashy Stuff
08:18 Keeping the Same iPhone
09:47 Free Flights With Points
11:29 Spending on Health
13:45 Fast Decisions Minimal Thinking
15:07 Experiences Over Luxury Hotels
16:56 Real Estate Stays Offline
17:47 No Family Rental Background
18:52 Dropping Out to Build Business
23:29 Working Since High School
27:08 Money Lessons From Parents
28:56 Hiring and Delegation Struggles
29:43 Introvert in Big Groups
30:42 Wrap Up and Takeaways

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]

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 Thanks
01:02 Why Hire A Virtual Assistant
01:15 Dropping Out And Early Hustle
02:40 Scaling Co Hosting Then Buying
03:17 Cutting Clients And Refocusing
05:05 Delegating Low Value Tasks
06:53 Growth Plan For 2026
08:41 Offer Co Hosting Help
09:09 Documenting VA And Content Team
10:53 Health Journey Segment
11:24 DEXA Results And Goals
12:34 Training Diet And Progress
13:48 Wrap Up And Contact

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]

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 Intro
00:15 Done For You Service
00:41 Finding The Duplex
01:40 Negotiation And Walkthrough
02:33 Under Contract Numbers
03:13 Renovation And Refi Plan
05:13 More Deal Examples
06:10 Upcoming Florida Setup
06:44 Questions And How To Reach Me
07:30 Wrap Up And Next Videos

Where to reach me:

DM me on Instagram: the_bailey_kramer

Email: [email protected]