You're spot on with the age-- I'm 37. So if you don't mind me using you as the example here (and I'm sure it goes without saying but you totally have my respect and admiration for juggling all that), would you have made any other choices, say college, or what have you, had you known that your likely income would be $X and your likely debt coming out of school would be $Y?
I don't think that we as mid-30 somethings now, truly grasped the magnitude of our choices when we were 18 and I think that has only gotten prohibitively worse as the years have gone by. I know not everything in life can be boiled down to a simple risk vs. reward calculation but I think there needs to be more pragmatism woven in to how we educate our young. I can't begin to tell you how many times over the years I've had an 18 year old (hell, even some college grads) come into my office and not even know how to fill out a check. Now, if we're not teaching the absolute basics like that, how are we supposed to help that same kid make an informed choice as to how they're going to create the foundation for that future?
I also agree with this and yes, totally different topic, but I think college is going to look a hell of a lot different in a generation or two.