Reflecting on his work now, I think Illich's anti-institutionism was extreme and his alternatives are genuinely not compelling.
Deschooling Society's critique is powerful, and Learning Webs is literally exactly how I learned how to program. But, it's an entirely unworkable alternative for like 60% of students. If we deschooled, we would absolutely end up with a double-digit percentage of the population either illiterate, innumerate, or both.
If you're honest with yourself, Medical Nemesis is has some great passages but in it is also the germs of the anti-vaccination and natural healing movements.
His critiques are powerful but the answer is not deinstitutionalism. The answer is taking his Tools for Conviviality to heart when engaging with/through institutions.
Without conviviality, Learning Webs will become a "Platform" with blood-sucking silicon valley middle men taking a 20% cut on all education spending and gig worker teachers languishing away in poverty. Of course, Illich would just say SV platform capitalism is also an institution^1.
With convivality, even the most institutional institutions can become places for human flourishing (Illich spent his life in the Catholic church, after all!)
So, I love Illich's critique. And Illich was a genius, in the sense that he proposed online education 30 years before the internet was invented.
But deschooling isn't the answer.
Conviviality is.
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[^1]: which is one of the reasons that Foucault is worth reading of Illich resonates -- Illich always sort of grounded out in a no-true-scottsman when you point out his alternatives don't work. Foucault provides a more robust theory by explaining how power and institutions relate to one another.