[sfRattan]

> getting a tantalising glimpse of what might be possible if only you weren't so timid/proper/responsible/considerate/whatever.

I think that glimpse is only tantalizing, and Kerouac's types only magnetic, when the reader lacks a well developed theory of mind for other humans and only obeys laws and social conventions for fear of punishment and ostracism. If you can empathize with others, shedding that capacity is more a strange nightmare than it is desirable. On the other hand, if you are fearful of social and legal consequences, freedom from that fear is absolutely a seductive fantasy.