I think this is an absolutely critical point. From my own tutoring experience insight with troubled students usually comes only _after_ engaging many "bad" questions in a row. Usually I find that students struggle because they do not understand, or are not aware of, some fundamental fact about the topic they are studying. Once you answer the last "dumb" question, they quickly learn all the other stuff they didn't know, because they have a sure footing.

In the future I expect AI tutors to ask more questions of students to quickly identify where their knowledge gaps are (so they won't even have to formulate the "bad" questions themselves).