Living aboard? Where to start?
Excellent source of info is Beth Leonard''s book "The Voyager''s Handbook."
I agree with some of the other advice coming back to you - get out on the water some more before you sell your house or your car! Get out in a real blow (2 reefs in the main and a storm jib, can''t see the mast) and get out in some dead air too. Spend a day in the rain, at anchor too. Not reasons NOT to do it - just things that should be as much fun as reaching under chute in the sunshine with a cold beer (its ALL fun for me, and some one of these days I''ll be casting lines off for an extended cruise myself!)
Best of luck - you do it in 18 months and you JUST MIGHT beat me to the punch!