This is such a great analogy, especially for under-represented college students, college really is an entirely different culture. We see just as much stopping out of college for reasons that I would deem 'cultural' as we do because someone ran out of financial aid, or they couldn't do the course work--perhaps more, if students were being totally honest. I think there is a ton of merit to investigating this analogy!
Clint, hello from a fellow Iowan!! This is cool. We work a lot with students from inner-city neighborhoods, and for me I think this kind of connection is critical -- it really helps students to see that there is a better future out there and that it can happen to someone like them, not just to fake characters on TV. Are there ways you've found to engage those returning alums to help students with the transition between high school and college? At my organization, College Possible, we are trying to think about what meaningful role college students can play as near-peer coaches (so valuable!) while recognizing the constraints involved in college student lives as well as in volunteer management.