Make certain that municipal code, or HOA, allows for a vacation rental in the area you are looking. 

Are there states/cities you like to vacation to?

Of course, if they don't vacate the premises by the date they are required, you should take the necessary step to terminate the tenancy, whether by a 3 Day Notice to Pay or if they are a holdover, by delivering demand to vacate with notice that they are a holdover and owe double rent per F.S. 83.58.

(Max vacated rents - your monthly mortgage payment) = +/- net cashflow.

If an agreement can be reached, the landlord does not need to spend time and money on an eviction, and the tenant has an understanding of how long he can stay, or his business can stay, and the agreed upon terms, before vacating.

It is a vacation/wedding destination town and a retirement haven.

It was easier for new owners to vacate the units and find new tenants since FL is a landlord-friendly state and the demand was hign.3.

My wife and I have been casually looking in the area.STRs aren't our main goal, but she's an avid hiker so it would primarily be a vacation home if anything.

Looking to get into STR for a good vacation market (hopefully in PST or MST locations for my first). 

Whether you should rent vacation rental (short term) or long term depends on your goals.