Thanks for the replies!

I am considering racing, and my husband is sure to push me to do it if I get a cross bike, but I'm not dead set on it yet... Chicago is very flat, so the local courses have a couple of rolling hills, but not much in the way of steep hills. I would probably do quite a bit of road riding, and a little bit of trail riding.

Regarding race support, there is no neutral race support. There's a wheel pit and that's it.

I have a compact double on my road bike (though I'm not sure of the numbers), and that works fine to get me up most hills in the area... so it sounds like a 10-speed would be okay (based on Velogirls comment) and would make switching parts a lot easier? Especially if racing and using the wheel pit, right?

Thanks again for helping me figure all of this out!