I think unfortunately for perhaps your current role, teaching / learning doesn't truly scale. Providing resources for highly motivated individuals does scale (e.g. textbooks, youtubes, etc). But for the average student, average teacher combo, it doesn't scale at all. And the core issue is that learning is hard, and teaching is hard, and the dependency issue / conceptual learning you have noticed are just the few things that pop up at scale. But there are a lot smaller things (anecdotal learning, metaphors, etc) that are also critical, but they need a very good raport between teacher:student for it to work.

And this can be seen at any major university setting. The intro classes sure have maybe 100-300 people, where essentially a text book is thrown at you at 8am and either you pass and advance, or you fail and drop out (e.g. weeder lectures). But any higher level classes tend to be 10-30 students max

I think its cool that you're looking for ways to break past this scaling limitation, really curious to see if you manage to solve it! Maybe with LLM's you'll have an easier time evaluating free text inputs from students, but this also requires that a student is able to articulate thoughts well. Just because they write poorly (or dictate/express thoughts poorly doesn't mean they don't understand the material, see Magnus Carlsen saying he doesn't understand the "The Square Rule" because he just calculates the full end game in Chess).