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.