I'm assuming your location of "Windy City" means Chicago?? If they sand the streets in the winter, a possible concern for using a travel agent is sand getting between the pulley and frame and locking it up. You'll be able to brake just fine if that happens, but the return spring may not have the strength to overcome the grit to pull the pads back off the rim. Even with fenders in MN, it's been a problem for me with my road tandem during the summer in wet conditions when the wheels/passing cars pick up winter sand and splash it into the travel agents. We've had to stop and flush it out with water bottles. I'm toying with replacing the V-brakes with canti's, as I've had no problems with canti's on my other bikes.