While I find him truly interesting, there is an annoyance: he is strongly critical about "traditional" school system, while holding a PhD himself. I've always found this kind of thing somewhat controversial. I wonder if he did consider dropping out during his studies; and if not, then why.
It somewhat feels like first getting the most out of a (by and large still hugely beneficial) system for your own good -- and then stating that actually, this is a remarkably harmful system.
(Side note: I read "Deschooling Society" quite a while ago; might not remember the main ideas all that well, so please correct me if this feedback is too harsh, or superficial.)
In that light, guys like the Finnish ecophilosopher (and fisherman) Pentti Linkola [1] seem more "true". As in, Linkola was heavily critical towards contemporary schooling, but he also dropped out of university at an early stage of his studies already, and (as much as I understand) lived in a cabin in the forest his entire life. It's a different path than first finishing a PhD and then becoming a notable critic of "the system". I don't think Illich would've had the same analytical capabilities and intellectual horizon if he would not have trained his thinking in a doctorate program.
Then again, Pentti Linkola's father was rector of Helsinki University, and also member of the Finnish Academy of Sciences and Letters. So I imagine Pentti the son was steeped in sciences and academic thinking at an early age already. Who knows, maybe that's what made him suspicious in the first place (no illusions?). A biography of Linkola is also published in Finland, but haven't read that one.
I will definitely read more of Illich, though. He is really clever and to the point in oh-so-many things.
0: https://www.goodreads.com/book/show/253081.Ivan_Illich_in_Co...