Well...
Yours is a bit different story.
Most guys living on a boat seem to have been married and chose to live on the boat that they already had during their marriage.
First step is to go into this with your eyes wide open. Boats require more frequent repairs than a land home.
If you want some real insite into the lifestyle I’d join the liveaboard boats facebook group and visit
www.liveaboard-boats.com These are sites/groups dedicated only to liveaboards on any style boat.
Then when you narrow things down to a trawler style boat, the guys here are the best at helping you choose one.