im heading down to pitt friday as well.
if you are into hip hop, my buddies are having their album release party friday night at the shadow lounge. couple live performances. should be a good time. if interested, let me know and I can get you more info.
also, make sure you eat at Primanti Brothers. The sandwiches are the best!!
Waterfront is cool for shopping. South Side is lined with shopping and bars/eateries. Station Square is cool as well. They have Hard Rock, and a bunch of other eateries/clubs/shopping. Strip District is a good party spot as well.