Hell, I know the goal is quixotic, but I will try my best. You are right in that going to UChicago is an excellent first step.
I forgot where I read it but graduates from top 15 doctoral programs aren't facing the professorial cutbacks as much as other universities are (or any real cutbacks for that matter). Considering UChicago is a feeder school into those programs—hell, maybe if I'm lucky I could go there for grad school—I have step one down. I understand I will need to push my self to my absolute intellectual limit, but if it pays off in the end, it is worth it.
That being said, I am not looking at UChicago as a means to an end. The school is phenomenal, the people there are smart, and I will have an amazing time and a wonderful four years. It will suck sometimes, but that is what one needs to put up with when going to college in general. I really can't wait.
Good luck in your finals Cedar!