I love books a lot, and I like to think that I like them "deeper" than most people– I reread almost everything I like at least 2-3 times. But yeah, 100 re-reads is something you only do if you're goddamn hell bent on deconstructing it. (I haven't yet found a book I feel that strongly about.) Otherwise you're probably better off reading more books and getting more context.
I've read Catch 22 at least 100 times. For a while it was the only book I owned(well, had in my possession). It's easy to just flip to any chapter and read it as almost a short story. When you're no longer caught up in the plot books seem a lot more enjoyable. It's also nice to never get that feeling at the end of a good book where you miss it.
I just realized that now that it's been a few minutes since I read the article, my take-away was actually "there is a lot of value in re-reading books", rather than "you should read some books literally 100 times". I'm not sure which was supposed to be the take-away, but I think the former makes more sense than the latter! So yeah, re-reading books you like 2-3 times is a great and enjoyable exercise.
