There's an old train station (historical, forgot the name) right on the Monongahela, across the river, near the Incline, that was renovated many years ago and turned into a fashionable mall with some bars and restaurants. Haven't been to Pittsburgh in many years but I did go to this place when I was there and noticed quite a few tasty ladies in attendance. But I do agree with your assessment of the city. I have a lot of history there and although the city has come light years from the old steel mill days, it's still somewhat of a grey depressing town.
One of my fond memories (and there are quite a few) of the city is being at Forbes Field and watching Roberto Clemente throw a perfect strike from the warning track in center field to put out a runner.
Gavy, knowing your appreciation of the "young" ladies, next time you might want to do a drive-by on Fifth Ave near University of Pitt. That area caters to the univ crowd and there's lots of bars around there.