Here's my take on this as a fellow Chicago winter commuter. I built up a touring frame (the Nashbar aluminum) with cro-moly fork to be my all around commuter, touring bike. I don't have the money or space for multiple bikes so I had to make a Swiss Army Knife kinda bike. I run cheapo Tektro V-brakes that came off my Scattante parts donor bike. I originally had a flat bar on the Scattante, but switched it out for a basic Easton drop bar. I run Shimano bar end shifters and Cane Creek Drop V brake levers. I think this is an excellent setup. I run SKS Bluemells (aka Alley Cat) fenders and 700x32 Vittoria Randonneur tires right now. The only interference I get with the brakes and fenders is that the little metal piece that holds the noodle rubs slightly across the tops of the fenders. I could lower the fenders down slightly but the metal piece barely touches and it doesn't seem to affect braking force. When my rims are clean and my pads are in good shape I can lock up and stop on a dime. Right now my rims are dirty and my pads are shot, so I really have to clamp down to get that stopping power. I'm not a huge fan of my Easton bar on the touring frame, so I'm looking at this bar for a replacement:
http://ritcheylogic.com/dyn_prodfamily.php?k=448376 Just another variation of the Salsa Woodchipper, except the Ritchey has a Randonneur/touring type of layout with the slight up-sweep at the ends and a slight flare backwards that puts your elbows inwards more than traditional drop bars do when you're riding on the flats. I like drop bars much better for Chicago riding, because you have the option of getting down in the drops to help combat those all to frequent headwinds. However, I don't like really deep drops like what you have with traditional road bike drop bars like my current Easton bar, hence the forthcoming switch to the Ritchey bar which has much shallower, and thus closer drops. Finally, I've done some checking and I will be able to run 700x32 studded tires with my frame/fender setup with no problem, so when the ice finally arrives I can still ride.