Great advice, everyone! I've been eagerly checking back here to see what you people have to say, and you've all been so very informative and helpful.
Right now, I'm leaning toward Breckenridge, mostly from the comments I've read on here. Great town, great skiing, and the Breck/Keystone/A-Basin ticket looks unbeatable. I've skied Telluride before, and I love the town and scenery, so that's also a consideration. Also, the advice to get a part time job for the sake of becoming a true "local" is really interesting... I hadn't considered that aspect before, but now it doesn't seem like waiting tables a few nights per week is such a bad idea.
What's especially encouraging is the positive responses from everyone. I expected the typical "stay in school, graduate first, crazy kid" response from a lot of people, but the fact that everyone has had only positive stories to share from their ski bumming days makes me all the surer that this will be an amazing experience. Now, if only I can convince the parents so easily... but hey, taking a year off to go skiing is the type of solid plan that _no_ reasonable parent could object to, right?
I still have another year to go before I take off, so I'm sure you'll be hearing more of more of me, as more questions are bound to pop up. In the meantime, I've gotta grit it out through the rest of the school year and try to keep my thoughts here in Massachusetts, rather than in Summit County. I can already tell, this upcoming winter is going to be like torture! Anyway, thanks a lot everyone.