Do you absolutely have to live aboard?
I'm curious because I'd imagine that, from your description, you'd take a pretty massive financial hit.
It's not just the cost of the boat. The restrictions that living aboard
would put on your work have got to hurt...
My apologies if the following offends. feel free to read no further and to put me on ignore.
Reading between the lines your job is driving you bonkers, the living options are driving you nuts and your social situation is driving you bananas?
Without saying these are must dos some suggestions (other than change jobs, find somewhere better to live or to find new friends) are :-
1) Work 6 months on, 6 off, year on year off, 3 years on, 3 off. This could be the most common solution.
2) Build model boats
3) Buy a small trailer sailer.
4) Take holidays in some of the more exotic locations.
5) Learn a foreign language
6) Join the peace Corps
My apologies again is this is out of line.