I’ve read most of this stuff, and even attended a speech by Ginsberg. I’m left with the feeling there was nothing to understand.
As for Kerouac, the artists he tried to emulate like Céline and Charlie Parker (think improvisation) were worlds beyond him. He knew enough to be infatuated with great artists, but never really synthesized some great literary voice, as he thought. I think he simply didn’t have the intellect. Perhaps it was all the “tea” he smoked.
In the end, he was just a French-Canadian from Lowell, MA who went to Columbia on the G.I. Bill and fell in with some pretty funky people. Had his literary attempts ended up moldering in his mother’s attic amongst vapors of ragout de boulette, the world would be no more the worse off–but then again, we wouldn’t have that Snack Attack song from Godley and Creme, and that would be a shame.