I live in Sarasota County (outside of Sarasota City), FL and trying to understand the rules, regulations and loopholes with STR properties.

Ensure you understand property laws, taxes, and local regulations.

Too many arcane rent control regulations to trip you up.

Backup Withholding: If a contractor fails to provide a TIN or gives you an incorrect TIN, you may be required to withhold a percentage of their payment for federal taxes (known as backup withholding) and remit it to the IRS.Following these steps will ensure you are in compliance with IRS regulations and avoid potential penalties.

And STR is much more involved with high turnover rates so you’ll not only need to post the listing but know how to keep it competitive so that you maximize bookings, of course, furnishing it, keeping supplies, restocked, cleaning, maintenance, And what about consideration to any local STR rules and regulations?  

Have you gone to the state, county and/or city websites to search for any STR rules or regulations?

Any regulations, limitations, or potential that you have uncovered and would feel comfortable sharing about.

Entire industries have left the state due to inept state and local regulators. 

It's funny how nobody demands regulation to make Escalades more affordable....... 

This country has the toughest regulations when it comes to Equal Housing Opportunity for the most part, except when it comes to convicted felons.