When Every Door Closes: How We Helped a Florida Seller Navigate an HOA Nightmare

Let me walk you through a recent situation Cody and I dealt with—it’s a real example of how even when every strategy fails, there’s still a way to pivot and help someone in trouble.

Back on May 30, 2025, one of our Florida clients—we’ll call her Monica for privacy—reached out saying she had just sent her Power of Attorney to the mortgage company. The home was sitting vacant. High mortgage, no equity, and some of the most restrictive HOA rules I’ve seen in a while. This wasn’t our first rodeo, but it was definitely shaping up to be one of those head-scratchers.

June 2–3: Monica let us know she was still waiting to hear back from the lender. By June 3rd, we got some hopeful news—she wasn’t in foreclosure yet. The loan was in “unemployment forbearance,” meaning the bank wasn’t actively pursuing legal action. She’d have a case manager assigned, and she had a window to work with.

Cody and I jumped in, digging into every exit strategy we knew. We checked the numbers. Tried to crack the code on short-term rental, corporate housing, PadSplit, subject-to, even lease options. I pulled up the full HOA bylaws and literally read every page—twice. I wanted a loophole. I was begging for one. But nothing. The HOA was airtight. No short-term rentals. No creative subleasing. Not even a squeak.

June 4–7: Monica was anxious. Rightfully so. She needed cash, and fast. She was holding on by a thread, keeping the power and AC on, keeping the house clean, but the clock was ticking. She offered us the lockbox code to make things easier.

We assured her we were reviewing everything, but between a family emergency on my end and just the complexity of the deal, it was a slow grind. By June 9, she was considering listing with another agent. I get it—desperation doesn’t wait.

We regrouped as a team and asked her to hold tight while we looked deeper. We got her full legal name, verified her POA for another family member, and confirmed the property was free and clear for us to start the contract process.

June 11: We sent over a contract. Monica had more questions than we had answers at the moment—and she was not shy about voicing them. “Is Graystone the buyer? When do I get the $25K? What’s the real plan here?” She wanted a clear date and a real commitment, not a vague agreement and empty promises.

And honestly? She had a point.

June 12–13: I offered to jump on a call to explain everything in full. That’s how we do it—human to human, not hiding behind WhatsApp texts or emails. We missed each other a couple of times, but eventually got on the same page. She signed the contract, and we got the green light to begin our marketing efforts to help her exit.

June 16: That’s when the HOA drama took a turn. I called the HOA myself—read the docs front to back again. Nothing about Airbnb or VRBO bans. Monica sent over her copy too, just to be sure.

But here’s the problem: even if the docs didn’t outright ban short-term rentals, the community rules were tight, and enforcement was strict. It wasn’t a legal problem—it was a practical one. We weren’t going to be able to sell this house as a cash-flowing short-term rental. Not in this community. Not with this mortgage. Not with this equity.

June 18, 2025 – That was the day I had to get real with her.

“Monica,” I said, “I’ve looked at this from every angle. And I’ve got to be straight with you. We’ve got two plays—and that’s it.”

Here they are:

1. Short Sale

We go to the bank, start the paperwork, and try to get approval to sell it for less than what’s owed. If we get lucky, Monica walks away with $10K and a clean slate. Not fast. Not fun. But a clean break.

2. Rent It As-Is

Keep it rented just enough to cover the mortgage and hold the line. No fancy strategies. No big cash-out. Just survival mode. Find someone who’s willing to roll the dice and take over payments in hopes of better days down the road.

That’s it. No magic bullet. No “flip it for profit” play. Just real talk and damage control.

Sometimes, the win is stopping the bleeding. Sometimes, all you can do is buy time, hand it off to someone else, and move on. Monica’s case was a reminder that real estate isn’t always glamorous—but if you’ve got the right team and a little creativity, even the ugliest deals have a path forward.

We’re still in this with her. Wherever she decides to go, we’ll move fast to support it. That’s what we do.

Keep it consistent, stay patient, stay true—if I did it, so can you! Ready to connect and strategize? Contact me at http://graystoneig.com/ceo – Jorge Vazquez, CEO of Graystone Investment Group & its subsidiary companies and Coach at Property Profit Academy.