Really great to read those responses, guys. I elected to click the "I'd prefer to be a Feb" box on the Middlebury Application, so everything mentioned confirms what I suspect about the Feb program.
The few reservations I've had about the program are getting into year long actives (clubs, whatever) and the certain classes that might be better suited as a year-long situation (foreign languages especially). I'm also a little worried about the prospects of studying abroad, as well as potentially getting stuck with an upperclassmen roommate (although the Midd webpage seems to say this is unlikely).
Again: I love the idea of the Feb kids as a small group within the college, and I love the idea of having the compromise between starting in September and taking a gap year for traveling/volunteering. Just some nagging concerns, is all. If either of you folks has input, I'd be thrilled to hear it -- if you're more comfortable chatting via PM, I'm fine with that also, but I imagine there will be a few Feb kids prowling the boards in the coming months that might be interested in reading your responses, too!