Thanks everyone, for the input thus far. Very helpful, especially for someone who's never really given much thought to a bike. My last bike purchase was a "oh, I like that one" *click*. This time, I'm really trying to learn all I can and research everything so that I feel confident in my purchase.
After test-riding bikes, I thought the Cross-Check was probably the most comfortable, but every so slightly. The aluminum frame bikes were also very comfy, and I was wondering if there were bikes out there that have the same geometry as the Cross-Check, but are aluminum instead of steel?