I think work is the big issue with this sort of lifestyle (leaving aside children, as others have mentioned). Many remote gigs still want a daily standup, a weekly sprint retrospective and planning session, etc, and none of that really works if you're truly nomadic and can't really guarantee where you are or how good your Internet connexion is at any given time.

The article talks about the flexibility of his lifestyle: "instead of following a fixed plan, I get inspired by random ideas: When the waves are great, I go surfing. When it’s chill and fresh, I work. When it’s hot, I go for a swim." ... which sounds lovely, but I can't see how that works with a full-time job, to be honest.

There are, of course, freelance jobs you can do where you have a task to do and a deadline and (hopefully) not too much real-time conversation required... but it may be hard to get enough of that work to support yourself.