about the winter shoes: there is a guy i've ridden fixies with in the past who is very into getting the best of the best gear-wise (don't worry, he has good taste and is a talented, avid rider) and i seem to remember him speaking highly of the sidi winter boots and also i believe the northwaves. for my money, though, i'm all about full fenders, regular spds lined with plasitc bags, wool socks and maybe some toe covers.

EDIT: last winter i used the shimano spds with the lace-cover flap and they seemed warm enough most of the time. just build up enough of a fat layer that you don't feel the cold. besides, you're not in montreal anymore! we don't get winter here...