I'm skeptical. I feel like there's an instinctive lunge from "these people irritate me" to "this is detrimental to society." In any case, you'd be writing off a fringe that has yielded quite a lot of stuff that I do like... like rock n roll. There is a definite connection there to the old "tune in drop out" mentality. The Beatles were some friends basically rejecting the rat race of their time and day, punk rock and hence most of modern pop, etc. Artists have always been receptive to subversive, diogenes-like ideas.
A lot of hackers from the early microcomputer days were rat race rejectors too.
As you close in on examples, it gets harder to generalize. Dude might be comparing himself to Diogenes, but I'd wager their motivations and ways are pretty different.
Everyone row in the same direction is a bad analogy, IMO, for large societies. We need contrarians.
I would estimate that they themselves would probably identify with some of these tangping people.
Spending long hours hacking computer systems, dressed in ripped jeans listening to Pink Floyd only looks like work in retrospect. ATT, much of it probably looked like an overindulgent hobby. Same for hanging out and playing guitar.
Diogenes himself left quite a legacy. Pretty direct line from him to stoicism, for example.
Most bummy subcultures don't become the Homebrew Computer Club, Beatles or whatnot. Some do.