I ride in the Dirty Dozen (
www.dannychew.com) every other year, so I'll be there in November of this year. Lived there from 1993-2002 and owned my own window cleaning business. Almost every business in Oakland I served at one point or another. 'The Original' was a mainstay of mine. Try the french fries...they're epic. The Beehive in the Southside is a cool coffeehouse hang.
Also, there's a group of cyclists on the down-low that do urban assault pretty often, but you'll need a suspension mtb, because part of the route is .5mile of rr track crossties. I tried the rout on a hardtail stiff fork and almost vibrated my fillings out. Pittsburgh has some of the loosest, no bs, straight ahead cyclists you're likely to meet.
Get yourself plugged in and you'll be plenty busy. Between the hills and the bridges Pittsbugh's a cyclist's dream.