Rental Properties: To Buy or Not To Buy? Why I’m Beginning to Reconsider

In my previous post, I wrote about stepping back from the “always buy” mentality and becoming more selective. Ironically, the very forces that made me cautious are also creating fresh opportunities—and I’ve started looking again.

Here are a few added considerations shaping my thinking:

1. Rate Cuts + Market Highs = Rentals Look Good Again

With the Fed cutting rates and the stock market hovering near all-time highs, traditional asset yields have compressed. Bond yields have come in, equity valuations feel stretched, and suddenly rental yields look compelling again. When income from real estate exceeds what you can earn in stocks or bonds with similar or lower volatility, the math becomes hard to ignore.

2. Rent Control Isn’t Going Away—Choose Markets Strategically

Rent control and housing affordability remain front-and-center political issues. The risk of new regulation isn’t disappearing anytime soon.The solution? Buy in lightly regulated markets or in places where population growth acts as a natural pressure valve. These markets tend to maintain healthier rent dynamics and are less prone to sudden policy swings.

3. Watch Short-Term Rental Rules: A Hidden Signal

Cities that haven’t regulated short-term rentals yet typically aren’t close to imposing heavy-handed rent control. And if long-term rental economics weaken, STRs can provide an alternative income stream.I recently did exactly that with one of my rentals—pivoting to short-term stays stabilized the cash flow almost immediately.

4. Student Rentals: Evergreen but Evolving

Student rentals continue to be one of the steadiest niches, thanks to predictable turnover and durable demand. The wrinkle: more universities now have large, purpose-built student housing nearby. Competition is rising, but the opportunity set remains strong. This topic probably deserves its own deep dive, and I’ll cover it in a separate post.

Bottom Line:The rental market isn’t a one-way bet, and the past few years proved that patience matters. But conditions are shifting once again. With the right geography, the right regulations, and the right rental strategy, real estate is back on my radar—and maybe should be on yours too.