Earlier quoted context omitted.
It's not hard to get a decent sail boat that would do the trick for well under $50k. For under $100k you're living large (literally). While that is not nothing, it's a heck of a lot less than we're all going to spent on rent (or mortgage) plus gas, car insurance, car payments, parking, house insurance, electricity, water and all the rest. "Cheap" is relative I guess.
There are plenty of people who have documented the actual cost of doing this over decades, to the penny. A couple catching their food, doing their own boat maintenance. $300k over ten years is the line below which you are arguably living homeless like transient vanlife, but on water - that is, living on the margins of society, on borrowed time. So buying a boat ($$), getting it fitted initially ($$), after that, mayb…
On the Pan-American Highway for two years I spent an average of $1,200 per month, for all expenses including SCUBA diving, shipping the Jeep (and flying myself) around the Darien Gap and everything else. That was 40,000 miles
In Africa I spent an average of $1,650 for all expenses including all National parks, visas, and all the rest. That was 54,000 miles.
I find it very difficult to believe sailing a boat with free wind power, free sleeping when at wild places and better access to free food costs more per day than driving a Jeep tens of thousands of miles that gets ~16mpg.