Re: I am 26, and seriously considering moving aboard with my girlfriend. Any advice?
Have a look at a Nonsuch 33 or 36 for a very comfy liveaboard and cruiser in your price range. We had an Espar heater when we lived aboard in NYC for two winters. We were much happier with our heating situation than people with electric were.
Heading back to Lake Ontario for this summer. Relatively few stops along the way from Grenada. Martinique, Guadeloupe, St. Martin (must have something to do with the French food), then Bermuda, New England and up the Hudson/Erie Canal. We were going to go via Newfoundland and Labrador but June remembered that one of the kids is getting married this summer - details, details!