Hey guys,
Another fixie freak in Toronto here

I work downtown, but for the last 5 years I had worked up an DonMills/Eglinton area and commuted on my 52/16 from the bottom of Yonge Street. Not a bad ride....I don't get out as much now because I work so close to home...I try to get a good half hour to an hour per day still...but its much easier when you have a longer commute!
As for the steepest Hill...For me there are a couple that are brutal.
1. Pottery Road
2. There is a hill off of ThornCliffe road (just off Overlea) that goes down into the Don Trails.. I have to zig zag down it otherwise my legs do a "fred flintsone"