My AirBNB cash flows anywhere from $600-2000 a month depending on season. 

Agree on the pool.  95% if not more of my cabin inquiries during pool season are pool related

Hi Steve, I'm also a newbie investor and found that going to my local investor meetup (Central Florida Realty Investors Association - CFRI) has been the best education as far as advice and tips, plus a great opportunity to meet seasoned investors in the Orlando area.

Also, most HOA don’t allow true short term rental minimum lease must be 30 days in most or could have to be seasonal cause some only allow 3-4 leases per year.

Most lenders will have some sort of seasoning period for cash out.

A lot will depend if there is going to be a second storm in the wake of Ian, peak hurricane season is still on at least until end of October. 

There may be some seasoning period for the change to take. 

Then I got a notice from the city forcing me to repaint the entire house during high season. 

Then when it has "seasoned" (usually 6 months to a year) and the bank will loan on appraised value, you refinance it. 

But over time we would expect prices in certain areas to reset to level out the premium of STRs relative to LTRs to reflect actual differences in management intensity, seasonality, and higher level of service needed for STRs and not simply the easy $$ arbitrage: "who knew there's people who will shell out $250 a night 20 nights a month for this place when i was only getting $1000 a month with this LTR?"