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Well, one of the potential difficulties here is the fact that students may have profoundly wrong or misguided impressions of what more advanced work in a field is actually like. It is always possible that deeper engagement and more first-hand experience of a subject will show them why they do not in fact want to delve further into the subject. Some will react positively to these new challenges and some will not. So at what point is it appropriate to honor such a response, even if it does express a wish for disengagement?

Your notion of boredom as a marker of a "productive inference range" is a nice way to think about this for individual students, but one of the trickiest things about the contemporary classroom is the diversity of levels and experience contained there, and the unpredictability of their responses to the challenges of classwork. So this becomes one of the most difficult things to calibrate as an instructor.

Since instructors are human, it's difficult not to feel personally insulted by the visible boredom of one's students, as I blogged about the Atlantic Monthly's Professor X some time ago.

http://long18th.wordpress.com/2008/05/26/blessings-and-curses/

This piece is about the tendency to blame one's students for one's own failings as an instructor. But learning how to gauge the effectiveness of one's teaching does require that the instructor learn how to become more reflective, and more responsive, about the students' feedback, both positive and negative.