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! :)
Having $4k to drop on a project is incredibly privileged.
Half of Americans don't have that in their account.
How is privilege or money relevant in any way?
Counterculture has nothing to do with either.
Used boats are (deceptively) cheap to buy.
Fiberglass hulls last forever. It’s everything else that needs repaired or replaced.