The lease was re-crafted when I purchased to add an appendix that strictly prohibits trampolines, pools, swing sets, and more. 

Siblings are not prohibited parties. 

Is there anything prohibiting me from doing this tax-wise?

I was excited to do research there but saw this article recently about "A Crystal River ordinance from 2005 prohibits residences outside the city’s waterfront-commercial zoning district to be rented out for less than three consecutive months" and I was concerned.

Checking with the engineering/public works department to see if they would allow for a dirt or gravel driveway in lieu of a full blown paved private road as it's cost prohibitive to build the full road right now. 3.

Addressing the LTR concern: both counties have used grants to boost low-income housing (in the form of apartments that prohibit STRs) rather than imposing broad restrictions.

While STRs might be off the table if your city prohibits them, MTR could potentially produce about 2x long term rents with the right property.

The REPS-9 election prohibits grouping short-term and long-term rentals, emphasizing the need for careful strategic planning.

I just read a post where someone purchased a STR in a town that recently prohibited STR. 

When I got back, I realized it was in a flood zone and the FEMA 50% rule would prohibit the rehab we needed to do.