The hardest part of any great books program is simply reading the great books. That sounds obvious, maybe, but it's extraordinarily challenging to read these works if you're not used to their styles.

I have made some progress on the classics and have been encouraging my son to do them using graphic novels as a soft introduction to them.

Discussion and lecture are important here, but I honestly think a good dialog with a frontier LLM would give you 85% of what's useful from those engagements.