As someone in almost the same position as you were in, may I ask a more personal question? Were you able to get into a prestigious school once you had money? I want to go not because I care about prestige or about connections, but simply because I want to find out what the experience is like, and know that I can stand with the best. I do online MIT classes for fun just to prove to myself that I can do it, but I never really had opportunity growing up, nor did I realize how much opportunity mattered. Now I'm concerned it's too late.

I'd love to get your thoughts. Please feel free to shoot me an email if you have ideas about how I might pursue this.