It seems you are out of touch with the liveaboard boat market. It's totally feasible to pick up a boat suitable for coastal cruising for a couple of people for $2,000. Budget another $2,000 for upgrades and you're good to go.
Any boat you pick up for $2000 will need $2000 just for new bottom paint. Then you can start addressing the rusted rigging and the broken inboard and the rotten sails and the failing mast step supports... why yes, I have been boat-shopping recently! :)
