Re: Please tell me this is a nutty idea so I will stop looking at this boat.
I spent a month on a 25 ft Hunter down in Florida doing the ICW and Keys. The wife and
I have spent many 3 day weekends on her as well. So you don't need a 30 footer. The biggest drawback of the 25 ft Hunter was no place to store a dink and a tad too much draft to wad comfortably to shore. If I was sailing the same area, the same way, I'd be looking at a swing keel/centerboard boat so I could beach her and step ashore dry.
No such thing as a free cat, and that goes for boats as well.