I'm curious, do the people who love the book generally believe that the characters in the story are admirable? I remember a certain sick feeling, the same you get with any story that pulls you along to places you aren't sure you want to go. But at the same time I could relate to the "anything but this" spirit it held toward the culture at the time. I appreciated the mood and the restlessness of it, like watching the sunrise after a regrettable night out.
It has been a long time and now I feel like I should revisit it to see if that still holds.
I'm not very familiar with Kerouac, but I've at least heard people talk about it. It was far less impactful, but reading the Scott Alexander review, the very first thing that comes to mind is SLC Punk! Of course SLC Punk! makes its message pretty explicit, and by the end the main character learns that living so hedonistically was always selfish / immature / destructive / etc.
When I was a kid, I was very sad for the last half of SLC Punk! Like so many stupid kids, I was sure that I was oppressed and my angry instincts had some sort of real defiance and valor to them. And of course, just like the movie, a bit of life experience and maturity revealed the lie. I rewatched the movie recently as an adult (~late 30s) it was a totally different experience. The end of the movie felt a bit like a mercy. (which I'm sure is what the director intended)
I say this only because I've never heard people talk about Kerouac in this way, but I also think the last time I heard anyone talk about Kerouac was back in college; back when we could still lie to ourselves about the nature of (stupid, teenage) rebellion. Back when we had no inkling just how selfish or privileged we were.