@Mario MoralesI'd look at the rental income and compare it to the cost of each situation to determine the return on cost.

In general personal homes are not optimal rentals.  

Although the rental increase will be modest, I am considering waiting until April 2025 to send the renewal, which would then start on July 1, 2025.

I am an investor myself and have purchased rentals that are all clean BRRRRs and 1% deals - positive cashflow, 1% rule, and tons of appreciation.

I listed it on FB marketplace as a Long Term Rental while it was under contract just to get the feelers out, and I got a lot of responses from people who wondered if I'd take Section 8.The house is in an area with pockets of Section 8 housing.

If you have a BAD tenant experience on this property as a rental and lose several months of rent and incur substantial tenant damage that is all coming out of pocket whereas if you had even a handful of rentals the performing rentals and the monies budgeted for capex/maintenance/vacancy will carry that sort of loss.

That will help you understand pricing trends for both the purchase but also the rental analysis. 

I would like to set up an LLC for my house, but there's not a lot of information out there on building a rental property in your house.

With the season in Sarasota County considered November - April, what is the best way to market the property as a Medium Term Rental (at least 30 days)? 

People will always have issue with shared amenities in a short term rental house.