After over 20 years in real estate, I've learned to listen when the red flags start waving—and this Naples condo is waving a few. I've dealt with properties like this before, and I've even gone through similar situations with my own mom. We had a condo where the HOA turned into a mini-dictatorship overnight—raising fees, changing rules, and making it nearly impossible to rent or sell without drama. It became more stress than it was worth.

Now, looking at your numbers—rising HOAs, insurance, flat appreciation, and only $500 a year in cash flow—you're not getting enough return for the risk or the headache. Even if you paid it off, you'd be parking a chunk of money into an asset that doesn't move the needle and is losing control to the HOA board.

If it were me—and I’ve had to make this same call with my mom—I’d look at selling and reinvesting the capital into a property where you’re in control. A nice single-family in a growing area, something with strong rent demand and better appreciation upside. You don’t want your hard-earned capital trapped in a place where you have no say and no leverage.  I actually wrote an article " the new dictatorships."  good luck.