I think a sense of humor is a significant attraction to most, but not all, in both genders. Some of these "looking for companionship" posts are just kooky enough that they elicit rough responses, but I didn't think this one was not all that bad. Just some lighthearted fun. I only notice one innuendo above, which is well below average (unless a bunch were deleted) and even that one I think was intended as a compliment, even a potential warning. Also, keep in mind that those looking for companionship can as often be predators, although, I doubt that is the case with this one. I've seen too many young ladies agree to go aboard a sailboat, destine for adventure, with someone they met yesterday. Warning Will Robinson.
Let's face it. Looking for companionship on the internet is a new era and it simply doesn't follow the same rule book we all had as a kid.
It sounds like the OP has a very attractive proposition. One which included a description of physical characteristics, I might add. She's doing the right thing, by looking for someone who shares interests. That's very important, for a life partner, in my experience. My suggestion, if nothing works out soon, is to move and reengage in a new sailing community elsewhere.
As a pitch, I think Narragansett Bay is one huge middle aged sailing hook up community.
Vermont is pretty limited, not proportionately many sailors in the first place, certainly fewer looking to sail the oceans. Around here you can join museums as a volunteer, teach sailing, volunteer at restoration schools or safety seminars, race or just help with organizing committees, its' literally endless. You'll meet more people interested in sailing that you can possibly remember names.