Yup, people living it dont brag about it, gotta keep the poser johnny come lately herds away from ruining it. I have been living and crusing on a sailboat, mosty off anchor rent free when I can, surrounded by many other sailors who rather not see it ruined by Instagram.
The key here is the counter culture starts and ends in your heart. Get out and break out of the matrix.
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! :)
The key here is the counter culture starts and ends in your heart. Get out and break out of the matrix.