Existing/older homes increased by 37.6% over the same period, or 7.5% annually.

In my humble opinion, I would start with a smaller project---60k sounds like a gut job and if it's an older house then expect it to be more once you start opening pandora's box. 

While I do tell people they should have travel insurance, especially planning a trip to SWFL during hurricane season, I also try to be understanding under special circumstances.  

It’s states …An occasional overnight guest is one who does not stay more than seven (7) days every six (6) months.Only persons 18 and older my be added to lease. 

Yes, look at properties in Galveston, 6102 Sea Wall Blvd, Galveston, this complex allows STR's, we can do STR no seasoning DSCR loans if you are interested.

But, when it comes time to put the deal together and pull the trigger: work with a seasoned real estate attorney with experience in structuring seller carry deals and writing thorough docs that cover your interests, especially with the "what ifs?"

It’s also worth understanding how they adjust pricing to adapt to changing market conditions and seasonality.

Seasonal Strategies: Any tips for maximizing occupancy and revenue during off-peak seasons?

Especially since there seems to be a lot of older housing stock as you point out.  

This is high season in Western NC.