I think that concisely encapsulated the two go-to solutions for so many hackers: a) create a complex system that will postpone or perhaps solve the problem; and b) make the problem irrelevant with a miracle stroke of genius solution to be fleshed out at a later date.

Totally agreed; this is exactly the generalized message I took away.

How many "lessons" (goals) could we tailor to the desires of the "student" (user) as a substitute for enforcement mechanisms? Surely not all, but many more than we're presently doing.