I had the dream to drop out and cruise. My wife didn't like the idea so we compromised and I got a cheap little catalina 25 to go sailing on instead.
Slip fees for that boat run around $450/month here in Toronto
Annual launch and haul out are an additional $600 +/-
Bottom wash, VC-17 and launch prep add on another $300 per year
Routine maintenance another $1000 per year easy. (lights, wiring, wash, pumpouts, battery maintenance)
Unexpected items add on another $2500/yr (complete re-rig, torn main sail, keel rebuild due to grounding, etc.)
As a hobby thats damned expensive, but as a house? Downright reasonable. I've often said that if I were a bachelor, I'd buy an old tub and move aboard, then let it rot in the slip. As long as I'm not paying for the maintenance on it and replacing sails and rigging, the boat is a free house, the slip fees are less than property tax, and around here they include water and hydro.
For my purposes, this would be just about perfect:
http://www.yachtworld.com/boats/1979/Morgan-46-2798069/Sint-Maarten-%28DUTCH-PART%29#.VfCTCxHBwXASell the mast and rigging for enough to patch-repair the FG, sell off the engine for more space down below. Sew some cusions, settle in and enjoy. If I ever decide I really do need to go see the world, I can slam a Volvo Saildrive through the hull and re-rig her. But more than likely, you'll find me at the yacht club bar.