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?

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.

In this episode of The Mid-Term Rental Show, I break down my most recent acquisition — three fully furnished mid-term rental properties purchased in a single off-market transaction.

What makes this deal unique is that I didn’t find it on Zillow…
I co-hosted these properties for years before eventually buying them from the owner.

I walk through:

• How the deal originated from an Instagram connection years earlier

• Why the seller wanted to exit — and how that created opportunity

• The exact purchase price, financing structure (portfolio DSCR loan), and seller credit

• Appraisal numbers, equity at closing, and total cash required

• Why I chose to move forward even though this wasn’t a BRRRR deal

• A costly mistake I almost made by using a non-standard contract

• Lessons learned from negotiating directly with a seller (no agents involved)

This episode is a real, transparent look at how long-term relationships, off-market deals, and understanding your numbers can lead to massive opportunities in mid-term rentals.

If you’re scaling your portfolio, transitioning from co-hosting to ownership, or curious how to buy cash-flowing, furnished rentals with tenants already in place, this one’s for you.

In this episode of The Mid-Term Rental Show, I break down a real, unfolding tenant dispute that’s pushing dangerously close to a lawsuit.

What started as a routine traveling-nurse booking quickly spiraled into claims of misrepresentation, mold, uninhabitable conditions, and threats of legal action—all despite prompt repairs, a full bathroom replacement, and repeated good-faith efforts to resolve the situation.

I walk you through:

• The exact timeline from move-in to escalation

• How small maintenance complaints can turn into lease-termination threats

• Why opinions ≠ legal grounds for breaking a lease

• The specific lease clauses (mold, habitability, late fees, attorney fees) that protect landlords

• How I’m handling rent refusal, legal bluffing, and next steps

This episode is a real-world case study on why strong leases matter, how to stay professional under pressure, and what every landlord—especially mid-term rental operators—needs to know before something like this happens to them.

⚠️ Real estate isn’t always passive. Sometimes, it’s legal chess.

In this episode, I’m recapping the past week of my life and business while on a ski trip in Park City, Utah — and what really goes on behind the scenes when you’re running mid-term rentals remotely.

I break down:

• How I manage 10+ mid-term rentals while traveling

• A major bathtub renovation mistake that turned into a $2,200 lesson

• A tense contractor pricing dispute (and how I handled it)

• A bad cleaner situation that made me look terrible as a co-host

• An unexpected Blueground booking mishap

• Why mid-term rentals are not fully passive (yet)

• And a big win: signing my first Done-For-You Mid-Term Rental client

If you think real estate investing means zero problems or total passivity, this episode is a reality check — and a roadmap for how to handle issues without losing your mind (or your vacation).

Interested in 1 on 1 coaching? https://www.midtermstrategy.com/1on1coaching

Interested in a Done For You Mid term Rental? https://mtrturnkey.com/application

In this video, I break down a real, side-by-side comparison between:

• Putting $39K into the S&P 500

• Using $39K as a down payment on a mid-term rental

I walk through:

• Stock market returns vs real estate returns over 3 years

• Cash flow vs appreciation vs tax benefits

• How depreciation and cost segregation changed the math

• Why real estate returns aren’t just about cash flow

• How one rental helped me buy more properties

You’ll see exactly why I chose mid-term rentals — and whether this strategy makes sense for you.

👇 Drop a comment and tell me which you’d choose: STOCKS or REAL ESTATE

In this episode of The Mid-Term Rental Show, I sit down with Adrienne Green — real estate investor, private lender, and founder of a virtual assistant staffing company — who’s built a business that lets her live and work from anywhere in the world.

We talk about her journey from corporate finance and teaching to real estate investing, scaling with systems, hiring virtual assistants, and eventually traveling full-time with her family across Latin America, Asia, and Europe.

We break down:

• What finally pushed her to escape the 9–5 grind

• How she scaled real estate remotely without burning out

• Why hiring the right executive assistant is a game-changer

• The mindset shifts that allow people to take real risks

• How systems + leverage create true location freedom

If you’ve ever felt stuck, overwhelmed, or curious about building a business that doesn’t tie you to one place — this episode will hit home.

Connect with Adrienne

Instagram: https://www.instagram.com/arealgreen/

In this episode of The Mid-Term Rental Show, I break from the usual tactics and numbers to talk about grit, risk, and belief — inspired by an unlikely national championship run from the Indiana Hoosiers.

Indiana didn’t have five-star recruits. They didn’t have the biggest budget or the flashiest roster. What they did have was relentless work ethic, a coach willing to bet on himself, and players willing to risk it all when it mattered.

I draw parallels between Indiana’s rise, Curt Cignetti’s journey to head coach, and my own path — dropping out of college, taking unpopular risks, and grinding my way into real estate and mid-term rentals without a safety net.

This episode isn’t about having the best resources.
It’s about doing what others won’t, trusting yourself when no one else does, and going all-in when the moment calls for it.

If you’ve ever felt like an underdog — in real estate, business, or life — this one’s for you.