<p>Certainly, debt vs. Oberlin is a really personal choice and no one (let alone me) looking in from the outside can tell you what you should do. Debt is frightening, and if you'd spend time at Oberlin worried about your future finances or the strain on your family or whatever--well, no school is worth that added stress when there's a viable alternative. And you have one, in TT. That said, though, it sounds like you'd really like Oberlin, and there is <em>so much more</em> to the undergrad experience than grad school acceptance. Sure, where you go to undergrad may not "matter" in the cosmic scheme of things, but it does matter in terms of your happiness. I'm not saying you'll LOVE Oberlin (who knows?), and it could be that TT turns out to be great--certainly, you can do a lot to make that the case--but being at a college where you feel like you "fit", where it's easy to meet people you click with, is so important. My vote, then, is for Oberlin. </p>
<p>That said, it seems <em>extrodinarily</em> unlikely that TT would ever hold you back in the long run in terms of grad school admissions, job opportunities, or alumni connections. I'm sure you'll flourish at whichever school you choose.</p>
<p>Best of luck!</p>