For those that spent a lot of money on an elite college, do you ever regret your decision?

The New York Times has been publishing a lot of articles and op-ed-blog posts about the value of higher education, which has included some discussion about the value of attending a top-rated undergrad institution (let’s say, within the top 20 for universities and liberal arts colleges in the US News annual rankings). For the purposes of this discussion let’s disregard the choice of one’s major. The consensus (among the writers and commenters) seems to be that “of course it’s worth attending a top-tier school, so long as you can afford it (and the same would go for graduate schools, etc.); if you can’t afford it, then just do really well at a public undergraduate school and then try to get a fully-paid graduate education! (as if anyone would contest that)

I suppose my question is two-pronged: the first prong is directed personally at those who possess the personal experience of having attended a top-tier institution and have the ability to thoughtfully reflect on the value it has conferred on their post-graduate years. Do you regret it? The second prong is directed at those who did not attend an elite college; “at the end of the day,” do wish you would have attended one?

I wish I had gone to a less selective school, had accrued less debt and been able to go to grad school without tripling my undergraduate debt (and perhaps committing the same error twice, i.e., attending law school), made less-snooty friends, and perhaps gone to school where I ultimately wanted to end up living, so I’d have more connections and more of a social scene where I am now. I’m curious if anyone else out there has experienced similar misgivings about designer educations, and how the rhetoric hammered into our high-school brains by parents, counselors and teachers about the importance of attending the best school you can get into, regardless of the cost (“education is priceless and any debt pales in comparison to its benefits”, etc.) was inherently overplayed and even detrimental.

For those who did go and regret it, how did you move on with your life?