I was in a pretty similar situation as you were. The bikes on my list were all cyclo-cross bikes:
Surly Crosscheck
Kona Jake the Snake
Specialized Tri-cross sport
Cannondale Optimo 3
I went with the cannondale after testing riding everything. It felt the best, can't really explain it. It's probably the least rugged of all but it seems to FLY up hills like a proper road bike. The kona felt really awesome in a different way. Really rugged and still fast but I liked the cannondale better. I don't think the cross check I road was setup right and the tri-cross didn't feel right at all. YMMV