I just got those two books from the library a couple of days ago. I haven't finished either yet, so I can't comment on them. One book that you didn't mention, maybe because you're from Canada, is Bob Mionske's Bicycling and the Law. I thought that it is a very good book. Well worth the read, especially if you are from the States.

I haven't tried one of those wool caps with a brim. I always thought the brim was not long enough to keep the rain out of the eyes. On rainy days, I just wear a baseball cap. On cold rainy days, I wear the baseball cap and a balaclava, either just on the head or pulled down around the face depending on the temp.