I can't imagine it myself. When I was cruising I got nervous just leaving the boat for a day! You know, walking back, hoping not to see just a mast tip or worse... nothing... and then... Whew, there she sits, just like we left her.
This is kind of a special circumstance, and I'm making the owner aware of the risks so that at least he can make informed decisions. It's possible that it may work out where he spends a shorter bit of time in The Bahamas and then comes back to Florida, for some of the reasons you are pointing out. In any case, we're probably talking about a year long cruise at most, due to health reasons.
Originally the owner wanted to take the boat to the Virgin Islands, but my feeling is that that's not practical. The boat is absolutely not outfitted for a two+ week offshore trip, likely pounding to weather much of the way; and a two+ month harbor hop (waiting for weather windows) is not really in the cards either. I suggested that if the Virgins were the ultimate goal, maybe charter or buy a boat there; whereas if having it be "this boat" was a major part of it (and it is), then perhaps outfitting/sorting things out in Florida and then a hop over to The Bahamas would be a more workable plan.
So, right now I'm checking out the options, and it's sounding like finding a marina/slip (if possible) might be a good one. It would be expensive, but then to balance it out the boat would not have to be *quite* so heavily fitted out in terms of energy systems and tankage (as opposed to when you're living on the hook month in and month out) so that could help to balance it out. Nothing is set in stone yet; just figuring out how best to work it all out.