We'll see how the calipers handle winter, but a lot of people I know in Chicago ride calipers through the winter and haven't had huge issues. The fact that I store the bike inside at night and in a heated storage area at work will likely help as well. I would have considered a Fantom Cross, but I already have a Surly crosscheck and it just seemed too similar.

The only big problem I see with the WT so far is a serious issue with toe overlap. Almost flipped the bike today when I made a tight turn at low speed in stopped traffic because my foot jammed the fender into the tire. Would have been scarry if I had been riding fixed.

I have planet bike fenders mounted over the 700 x 32 Kendas that came with the bike. With the front fender mounted using a "sheldon" fender nut (so the mounting point is behind the fork where it is intended to be), my clipless pedals almost touch the fender in the 9 o'clock position. I'll post a pic soon to show what I'm talking about.

I can move the fender mounting point to in front of the fork, which will probably help. Otherwise, I am going to have to move down to 28s--something I didn't want to do in the winter.