Re: Ideas and/or guidance
That would be a great opportunity to have. Personally, I'd save, save, save until I could buy a boat for cash, spend 4 months/year on it, and keep it on the hard the remainder of the year.
As for location, I'd probably do Florida for reasons mentioned above. It might be worth checking out some options in Puerto Rico. We've stayed in and sailed from Fajardo. San Juan was sorta sketchy, but Fajardo and the nearby islands are amazing.