Correct me if I am wrong, but you are suggesting the user teaches the AI or does the AI teaches the user? Or is it a mix of both(Eg the AI learns about the user drawing habits and style) Apologies, I would just like to clarify!
Because personally, I think the latter would be a great way for one to learn how to draw digitally. If we could come up with an AI that can "edit" and "correct" the user drawings, it would help tremendously in allowing the user to first understand the fundamentals and basics of digital drawings. I have tried drawing digitally in the past and one problem I faced was that while I was looking at many references/artist inspiration, I did not understand how to translate drawings on pen and paper onto the digital canvas. This AI can suggest brushes(their hardness/softness/colour etc) and their strokes on specific areas of the drawing to aid the user as they go along creating their work. Alternatively, it can also be programmed in such a way where it corrects the user drawing after the user has completed their drawing(sort of like a auto-enhance function in photo editing). This feature does not have to be fully automatic. For example, step by step instructions can be given on how to improve the drawing and it is up to the user to follow it. In addition, I think it be great to allow users to mimic the artistic style of their favourite artist. That being said, at the end of the day, the user should still have complete creative freedom and the AI shouldn't spoonfeed them all the way. We do not want the users to copy their references completely but instead use them as inspiration.