ON THE INSURANCE. That series of issues would guide his decisions.

Having a remote boat down there when he's in the NE is asking for emotional and/or financial troubles.

If he doesn't care if the boat sinks, is willing to deal with the after event issues of salvage, etc. -- then its probably not an issue. Otherwise, I think that would have to be a major part of his plan.

Off season slips down there are probably easier to deal with than In-season slips. I don't know how many full service marinas there are, but they can't be too plentiful.

My general view: For one season, all of the stuff you'd need to keep the boat up to minimal levels would seem to me to cost close-to what the extra slip charges would be -- even then, you're talking about systems that are best handled by a sailor that is around and can keep them working. Just getting the systems set-up and tuned would take a bunch of time.

My own concern for your unidentified sailing wannabe: If he's seeking relaxation, then having to get-up every morning and worry about your boat and what someone is doing to (on purpose or accidentally), or worry if the this held, that worked, etc. will not yield what he wants. If he's not ready to have the boat at least at a marina and secured at slip -- with a staff that will take care of him, then he's going to have a miserable year of hassles...or worse.