If the community is well-managed and there’s good rental demand, a condo could be a solid choice.

I don't see any reason why you would go to Miami, where the above problems are likely very similar, but there is even less cash flow to de-risk most investments, and it is not your backyard. 

You would end up saving the higher interest rate on the HELOC as well as closing costs.

I would suggest looking into syndications as well.

I am in the Port Saint Lucie, Fl market and i have an airbnb that is doing quite well from an income perspective. 

Perform this research by using the rent comp tool on BiggerPockets as well as FB marketplace, Zillow, Craigslist, etc Also for those 15% of units that are “at market”.

Ive been thinking about it as well.

If you are not already working with a realtor that is well versed in STR and knows ALL of the requirements for STR, do yourself a favor and reach out to @Josh Green.

We've seen robust demand in OCT (leaves) as well as NOV/DEC (snow chasers). 

Multiple people bid on that property as well.