Not sure how it holds up in this day and age but a common setup was to have 3 products: free, cheap, expensive.

The free one gets people in the door. Cheap is could be something like a book or paid tool or course. And the "expensive" would usually be consulting but could also be a more premium tool or retainer service.

So your suggestion seems to fit the model.

I know LLMs will change the developer education landscape but I really hope it doesn't kill it. Interesting times.

I think you mean free, expensive, and slightly even more expensive.

Depends on the audience and the niche

just because you can optimize your pricing for maximum value extraction from your customer doesnt mean you have to

That's a different model. Both are valid.