I've heard that the Sarasota County is in need of money (and that's the reason AirBNB deducts taxes and directly passes them to the County) - how strictly are those rules enforced? 

It looks like the Board outsourced part of the enforcement to a 3rd party company.

That said, "chickens coming home to roost" from the various seller-financing deals done WRONG is a very strong potentiality, as issues of such will most likely grow in occurrence and thus possibly press internal audit's that uncover such, and resulting enforcement actions start enacting in a volume.

Mitigate with deposits and enforceable lease clauses. 

While it is still your responsibility to get that enforced, you may then have legal grounds to seize their equipment and such. 

If they are VERY professional, they will have their processes in writing as verification that policies are enforced equally and fairly by their entire staff.6.

Look for distressed properties and motivated sellers.ProbateDivorceBehind in property taxesIn Preforeclosurevacant propertiesCode enforcement issue propertiesetc

If they are VERY professional, they will have their processes in writing as verification that policies are enforced equally and fairly by their entire staff.6.

The enforcement of these policies, and the reopening of the Center View Road Multipurpose Convenience Center, are expected to significantly increase capacity at the other 10 residential convenience centers for Sevier County residents.More information on the fee schedule, including the locations and addresses for all County convenience centers can be found on the Sevier County Government website: https://shorturl.at/p1gJE

Enforcement was definitely lacking in the past.