I went to Pitt as an undergrad and overall had a good experience there. Oakland is a fantastic place to go to school. It's such a vibrant area and as a student, I always found something inspiring about the energy of the area. (Although keep in mind that going out there at night is pretty much just for the young undergrads, we're too old for that area now!) I wouldn't live in Oakland though either. It's full of slum lords and loud drunk undergrads.
As far as living goes I'm a huge fan of the east neighborhoods (Shadyside, etc). In my opinion you should look into Bloomfield. It's right next to Shadyside and has very cool old homes that are now largely apartments and these are all spacious and well priced. It's very easy to get to Oakland from there as well.
I agree with Viva also...Pittsburgh is pretty damn dreary in the winter and things will look much brighter in a few weeks.