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.