I am personally quite envious of those who had the opportunity to attend prep school and elite universities. I think it is not necessarily the academic education that is important, but how one is socialized i.e. exposure to upper class sensibilities. I think these elite institutions also instil a sense of pride, confidence and "entitlement to succeed" in their students.
I went to a classic New England prep school (name like a law firm, anyone familiar can figure it out), and I'm not sure I fully agree with your characterization. While I found the education to be great - a fact I only fully realized when I got to college and read some of my peers' freshman year essays: yikes, paragraphs might be helpful - the exposure to upper class sensibilities was sorely lacking. We had the typical jock bullies, Latin club geeks, drama fops and cigarette smoking punk rockers. This was no finishing school - I've met kids from the PJs that are more charming, sophisticated and so-called "classy" than the Rockefeller descendants I went to school with. I won't argue with your comments on pride and confidence, even though it that can be detrimental at times. I think a big thing that these schools (and a privledged upbringing in general) can take away is drive. An entitlement to succeed is almost a sure guarantee of failure. The one thing I think these schools teach extremely well, without really meaning to, is social networking. You learn from the beginning that it's good to know people. And it's not necessarily the people you meet at the school - but rather how advantageous social networks can be in business and how to effectively utilize them. I know people who've been hired based primarily on their contacts - see any lobbyist in business.