it's been exactly 8 years to this day that i closed on my 53 and moved aboard. only two regrets are not having done it sooner and not having switched to sail back then
i was lucky to have sold the condo (2/2 on the bay here in miami) at times where you'd actually break even on real estate, it was just before the bubble (unfortunately...). Nowadays, your options are very limited and depend on your situation. If the house or the existing boat is paid for, renting the house and upgrading the boat can work but if you need rely on the rent to cover the house mortgage and taxes, or worst need to finance the boat then you are taking a BIG gamble and it can all go downhill very quickly.
also, some areas are not Liveaboard friendly so the first step so to research your area and see what your options are. by not liveaoard friendly i mean very few marinas or even jurisdictions which allow liveaboard.
finding the right slip/marina can be a little difficult as well as you will be a little more picky than you would with a non LA slip. Location Location Location is even more critical than on land; not only do you want a nice neighborhood but you need to consider exposure to wind and chop, view, etc... you also need to consider pier configuration and ease of boarding (finger piers often a must), accessibiilty to pump out (unless on board treatment is legal), etc...
i don't think i'd consider living aboard under 50' and certainly not with home comforts like AC, washer/dryer, full size appliances, etc... on a side note i disagree about Splendide washer dryer combo 'sucking'... i've had one for 5 years and it's fine. the vented model dries as well as stackable, the problem is with the non vented model. btw, the Splendide is NOT a marine/RV appliance, they're made in italy and very popular in european homes where washer/dryers are often installed udner counter in kitchens. obviously they are small so for a big family you have to do frequent loads
the Live Aboard forum mentioned above is ok but it's more like a Camp Aboard forum as most members live on smaller boats and frequent discussions include whether or not you can "live" on a 30 foot sailboat kept on the hook
