If they have money, they might buy to have control of the area.

@Miguel GarciaDisqualified parties who your IRA may not transact with include lineal family, so you, spouse, parents, grandparents, children, grandchildren or an entity controlled by those family members.Other family members may be OK for the IRA to transact with, so long as you are not creating any kind of indirect benefit to someone who is disqualified.

Do they (Florida government) have price control, property inspection, etc.?

There is a lot of opportunity as taxes are favorable and pricing isn't out of control (yet) You have to be careful which section you invest in though as the area is still fairly depressed.

You want to be in control of your rental unit (which is essentially a business) and investing in a property with an HOA is a huge risk since you are no longer in control.

The markets control rents and property prices but you must only make offers on a property that will produce cash flow regardless of the market.

Outsourcing to a company you have no direct control of is just not going to cut it.

Any buyer can walk in behind one of these frauds, make an honest offer, put down substantial consideration, and kick the unlicensed broker to the curb.From the statute:All contracts, options, or other devices not based upon a substantial consideration, or that are otherwise employed to permit an unlicensed person to sell, lease, or let real estate, the beneficial title to which has not, in good faith, passed to such party for a substantial consideration, are hereby declared void and ineffective in all cases, suits, or proceedings had or taken under this chapter; however, this section shall not apply to irrevocable gifts, to unconditional contracts to purchase, or to options based upon a substantial consideration actually paid and not subject to any agreements to return or right of return reserve

The property is close to 100 years old and is in rent control area.

Thankfully one of the residence is a real estate attorney and owns a property management company so he appropriately got the rest of the community involved so this didn't pass.But ultimately associations can have a lot of control over what you can and can't do with your rental and whatever control they don't have they could just make your life that much more hectic.I hope this information helps and gives you some food for thought.