Looking to Airbnb/vacation in Dunedin area

Hi All, 

I am interested in gaining some market insight, specifically in Dunedin, FL. The goal is to eventually purchase a pre-retirement, retirement home (not planning to retire for 10 years or so) - that in the meantime would be used for airbnb and general vacationing, or potentially as a regular rental as well. Any realtors, locals, airbnb-ers, etc in that area with insight would be great. I am located in New England, so if there are any glaring things to be made aware of prior to purchasing a southern home, or a home located near the gulf, or local airbnb regulations, general landlord friendliness, ease of hiring a management company/cleaners, necessity of flood insurance, etc, please feel free to let me know. Would likely be conventionally financed (open to other financing options, just saying this isn't a "I need to get in with zero dollars" type of question) when it comes to it. No rush to purchase, simply looking to connect with some local boots on the ground at the moment and gain an understanding of the overall market to help me make a good purchase when the time comes. I appreciate any help and insight. Thanks!