The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

Apparently some pretty sketchy people from that building are hanging out in front of mine which is scaring potential tenants away when our property manager brings them around.

., known for its upscale appeal and strong demand for vacation homes.Properties in the Hamptons attract affluent buyers and renters, offering a high potential for appreciation and steady rental income.he property may have been undervalued due to its condition, presenting an opportunity to add value through targeted renovations.

Cons - Risks as stated by others, can limit which renters are looking at your house. 

you not on one of the major listing sites you are missing a lot of revenue potential Penny wise dollar poor

I would say 225k around average to stay out of high risk zones.

Best advice is to learn from others and take calculated risks.

Most traditional property managers don’t handle this setup due to challenges like managing tenant disputes, coordinating overlapping move-ins/outs, and the risk of Fair Housing violations when selecting tenants.

Back home I would make a packet for my appraiser and never had a bad appraisal due to the that I specified the value add and the Reno amount and broke it down so they saw the potential and it always worked.  

Secondly, short-term rentals provide flexibility for owners, allowing them to potentially use the property themselves when not rented out.