Like tiny house owners, few boat people last long. I’d look into this carefully before trying it. There must be some associations for boat life people.
I do know some people who do boat life part-time, but they also spend 6 months of the year in the Bahamas, taking their boat there but staying on land. Such a lifestyle requires more money of course.
It mostly depends on how rich and old you are. And also on how much you like sailing. A small boat on a small budget will soon tire you out. A newer large boat can be a lot of fun. I know a couple that has been living on a 48’ sailboat in the Carib for the last 7 years and loving it!