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.
Back in the water in Grenada - with new main and #2 and cockpit canvas (Santa came early). Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.