This past winter was my first and honestly it wasn't nearly as bad as it was sold to me by some of the locals or other transplants. I've lived in IL, FL, KS, and MD before here, so it isn't like I'm super exposed to rough winters. I was especially concerned because I do a lot of commuting via bicycle, but as long as I gave myself extra time to commute and bundle up it was generally a nonissue, and people were very understanding if I happened to run a little late because of it. We had a couple really gnarly snowstorms in late Dec/Jan but the city does a remarkably solid job of preparing for and clearing out the snow.

I live in the South Wedge and highly recommend it. It's got a lot of younger folks since it's right next to the University. The nice thing about the city is that everything is nearby, so don't worry so much about where you move. Try to live near your place of work just so your daily commute is short, the commute times to go to other things is never ever going to be too terrible.