I actually did this for a while. I bought a sailboat with a friend, moved onto said sailboat, and bummed around for a bit. It's cheap in bursts, but then you need things. What happens when you have a sudden need for money, like an engine breakdown or a medical emergency? What happens when you suddenly need to travel, like for a funeral or a friend's wedding?

What happens when one day you need to afford anything beyond the daily living expenditures and you need to get a job and now employees side eye you for having a year or two gap on your resume? This is possible, obviously, but it's definitely a lot more than it sounds like on the surface.