Real Estate Horror Stories: The Hard Lessons Behind the Deals

[Brandon Kunasek]

Hey everyone,

I’m Brandon from Myrtle Beach, South Carolina. I work primarily in multifamily and short-term rental investing — and over time, I’ve had many conversations with investors about the unfiltered side of real estate: the deals that didn’t go according to plan.

Whether it’s unexpected costs, regulatory curveballs, or guest and tenant issues that test your patience, these stories always seem to reveal the same truth — the best investors aren’t just great at finding opportunities; they’re great at managing chaos.

Through my investor interviews and real-world deal analyses, I’ve noticed that every “horror story” tends to leave behind one valuable thing: a framework for better decision-making. From financing and management to due diligence and exit planning, every mistake becomes a case study in what to do differently next time.

I’m curious — what’s the toughest lesson you’ve learned the hard way in real estate?

Was it something financial, operational, or maybe just human nature showing up in your deal?

Let’s turn a few of those challenges into takeaways that can help the next investor avoid the same traps.

— Brandon