I wonder why Keruoac-like personalities are so magnetic, I never felt it click.
Maybe it's that people wish they would dare share that freedom? Escapism from boredom?
The lifestyle does not at all feel pleasant, at least to me. I don't mean it in the sense of regular comfort; these lines describe a tortured man more than they do a 'happy beggar'.
And then there's the chaos the trainwreck leaves behind. I don't believe a man that's truly passionate would have so little empathy for others. If anything, it feels egotistical and self infatuated.
I find the magnetism from these types of people is seeing someone violate your social norms (usually for gain) in ways you had never considered, and getting a tantalising glimpse of what might be possible if only you weren't so timid/proper/responsible/considerate/whatever.