You make a very good point. I'm highly biased as I'm doing it myself, but what I see from the people around me doing it is that most are not "bums".
Instead they're able to reduce their costs aggressively, that helps them spend time building startups/businesses and have a longer runway to do that until it becomes profit generating. The next step is growing and building more of those businesses. Many people I know generate $10-25k/m. You're right I know just as many that generate $500/m. But most of them are just starting. Most people are able to generate substantial revenue after awhile.
The next step for many is to invest in real estate in emerging markets. They rent it out or AirBnB it to foreigners. Then at 60, they're probably better off with more cash, more equity, than if they'd stayed in a place with high costs (e.g. US/EU right now). Most people in EU/US are simply unable to save money due to the rising costs of live (mostly rent and food).
I don't like how this is portrayed as the "this solves everything"-lifestyle. It doesn't at all. But if you take advantage of the cost thing, it can be beneficial.
> I don't want to discover at 40 that I have no close friends, no family,
That's also a great point. I feel the same and the only way we could be able to fix this is if this becomes more mainstream and you have friends doing it too, and make lots of new friends that are doing it. Technology also helps a lot (e.g. simple stuff like WhatsApp) to stay in touch. And most of these nomads are flying around every 3 months, so they do stay in touch with their close friends.
I'm excited to see where this goes, there's definitely many social challenges to solve.