Hi Tyler, that is quite a trek you have ahead of yourself, you will be in awesome shape after just a few weeks. The ride from downtown up to York U has a slight uphill grade most of the way, I am loathe to tell you, but at least the ride home will be fun

I've biked in Toronto for awhile and I think that the best idea would be to get some bombproff wheels as our roads could be in much better repair and you will be bouncing around a lot unless you get something solid. For winter riding, a set of fenders is mandatory, I think the Steamroller has eyelets for them, and I guess that you will be using some panniers, right?

You'll love the city, especially right where you are; that is Little Italy and it is a great neighbourhood to live in for a first-timer. Welcome!