Buying real estate sounds exciting, right? But then you run into three little letters that can change everything: HOA. Homeowners Association. At first, it sounds harmless—“Oh, they’ll cut the grass, keep the pool clean, and make sure the neighborhood looks nice.” But after 20+ years, 3,500+ deals, and living through the 2008 crash, I can tell you: HOAs can be one of the riskiest parts of an investment.
Let’s break it down in plain English, with a couple of war stories from my own life so you don’t have to learn the hard way.
What Is an HOA Anyway?
An HOA is basically a group of neighbors who get together, collect fees every month, and decide how to run the community. Sounds fine in theory. They take care of the pool, the lawn, the clubhouse, maybe even the exterior paint of your unit. You pay them, they take care of things. Easy, right?
Well… here’s the catch. You’re not the boss. They are. And when they say “your fees are going up,” you can’t say no. You either pay, or you risk liens, fines, or even foreclosure.
Why I Don’t Trust HOAs
After 20+ years and thousands of transactions, I can tell you I’ve never had a truly good experience with an HOA. Here’s why:
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They can raise your fees anytime. Cash flow is the name of the game in real estate, and unpredictable expenses kill cash flow.
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You’re at the mercy of other owners. Even if you pay on time and keep reserves, if half the building stops paying, you’ll be stuck footing the bill.
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They have too much power. Some HOAs even have the right to block your sale or buy your property first. Talk about a bad deal.
My 2008 Crash Story
Let me give you a real example. Back in 2008, I owned a condo in a community with an HOA. I was doing everything right—keeping my property in shape, paying my fees. But then the crash hit. People around me stopped paying their mortgages and HOA dues. The pool shut down. The landscaping dried up. The clubhouse turned into a ghost house.
Guess what happened next? My fees quadrupled. Yes—four times higher. Why? Because someone had to cover the shortfall. And that someone was the few of us still paying. It felt like I was paying for everyone else’s mistakes.
The worst part? When I tried to sell, the HOA blocked me. The bank approved a short sale for $25,000 (on a property I owed $120,000 for), but the HOA said no. They had the “first right of refusal,” which means they get first dibs on buying before anyone else. That clause turned my deal into a dead end.
So yeah—me and HOAs? We’re not friends.
The Myth of HOAs Handling Repairs
People often tell me, “But Jorge, at least the HOA handles repairs.” And I laugh. That’s like saying, “At least the dentist gives you free lollipops after pulling your teeth.”
Here’s the truth: repairs are part of the business. You want to learn how to handle them, because that’s how you level up as an investor. With the right team—contractors, inspectors, property managers—you can handle anything from a leaky roof to a busted AC.
In fact, I’d argue it’s safer to handle repairs yourself than trust an HOA. At least you know where your money is going. With an HOA, you’re writing a check and crossing your fingers.
Why I Love Single-Family Homes and Fourplexes
So what’s the alternative? I’ll tell you what I prefer:
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Single-Family Homes. No HOA bossing you around, no shared risks. You control your cash flow.
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Fourplexes. Want to go bigger? Buy a fourplex or two. You’ll have multiple income streams, but you’re still in control. No association raising fees out of nowhere.
And here’s the bonus: if you ever want to sell, tenants in single-family homes are way more likely to buy the property than condo tenants. Condo renters usually see it as temporary. But a family in a single-family rental? They can picture living there forever. You might even sell it to them at market value—or above.
The Problem with Collective Thinking
HOAs are built on the idea of collective responsibility. Everyone chips in, and the neighborhood thrives. In theory, that’s great. In reality, it only works if everyone pulls their weight. And let me tell you, in real estate, not everyone does.
When neighbors stop paying, the HOA still has bills. Guess what? You and the other paying members cover the slack. That’s not fair. It’s like going to dinner with friends, ordering a salad, and then splitting the bill when they all ordered steak and lobster.
Hidden Risks You Don’t See at First
Here are a few more HOA red flags most new investors miss:
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Special assessments. These are surprise bills for big repairs (roof, elevator, parking lot). You can’t avoid them.
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Rules that change. HOAs can suddenly ban rentals, raise pet fees, or limit who can live there. That kills your exit strategy.
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Foreclosure power. If you don’t pay, they can foreclose on you—even if you’re current on your mortgage.
What I Recommend Instead
If you’re starting out, focus on single-family homes. If you’re ready for more, go into small multifamily like duplexes, triplexes, and fourplexes. That way you get scale, but you still run the show.
Want to really scale up? Buy multiple fourplexes and create your own mini-apartment community. Guess what? You just became your own HOA—with you in charge.
My Bottom Line
So, is it a good idea to buy properties with HOA fees? For me, the answer is clear: No. The risks far outweigh the benefits. You give up control, you expose yourself to other people’s financial problems, and you lose the predictability that investors thrive on.
If you want long-term stability, predictable cash flow, and an easier time selling later—stick with properties where you’re the one calling the shots.
Final Words
Keep it consistent, stay patient, stay true—if I did it, so can you. This is Jorge Vazquez, CEO of Graystone Investment Group and all our amazing companies, and Coach at Property Profit Academy. Thanks for tuning in—until the next article, take care and keep building!
If you’d like to connect directly with me, feel free to book a time here: https://graystoneig.com/ceo.
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