No slab houses, age restriction too i.e. expectation to be paid in full before retirement.

Odds are, you would come out ahead by paying to have it managed and just continuing to work. 

We've thought about subbing out to a proper "property management" company but we really don't need help collecting rent or expenses (this is all done electronically online) or even finding new Tenants on the odd occasion when we have an Apt turnover (we use Brokers for that) ...

Take a look at your listing in incognito mode, you may find it has now been removed or made hard to find.Isn't there a way have your calendar open but to restrict your check in days to the first 2 weeks of May, or whatever you want?

The odds are slim but the victory would be huge. 

Woodstock area and the Catskills have STR restrictions. 

One other thing to note -- if you do end up doing all of the work yourself under an owner-builder permit, there is a restriction that the property cannot be rented or sold for 12 months.

Golf cart license are being restricted due to to many people, sinking foundations- either to close to unrestored sea walls or not enough pilings or fill dirt not allowed to compact, off grid experience, check on sewer and water infrastructure- when the water pump went out, the island shut down, the islands systems are being overloaded, what type of experience and thus rental rates are you shooting for?  

NACA doesn't restrict your refi or selling at all.

Odds price doesn’t escalate?