My biggest commute hill is Poplar Plains Rd, which rises 30 m over about half a kilometer, so about a 6% grade. I'm old and heavy and carry some stuff, so I'm slower than most youngsters.

You asked for inspirational anecdotes. Occasionally I do three or four loops up Poplar Plains and down the parallel street just for fitness. One time (true story, I swear!) some young people wearing shirts labeled "University of Toronto Triathlon Club" were doing the same loops, and to my surprise, I lapped one of them. Of course, it could have been her hundredth time around. Also she looked like kind of a noob, so maybe she had just joined the club and wasn't yet in shape.

One of the things I thought I might do for a challenge this summer is ride the 5 or 6 road sections Toronto cyclists have identified as the steepest in the city. They're all pretty tame compared to what many other cities have to offer. Most rise 30-40 m at grades under 20%. The toughest, but not steepest, rises 100 m in a kilometer.