These were the highlights of my trip:
* "The Strip" just west of the downtown core on Penn St. and Smallman St. between about the 1700 and 2200 block has recommended restaurants, some fresh food markets and nightlife. The restaurant Kaya here was a delight.
* South Side is an interesting neighborhood within about 20 minutes walking distance of Station Square "T" stop. There are alternative clothing stores, coffee shops and a mixed blue-collar-steel-town/artsy vibe that give this neighborhood a unique ambience.
*Take the Monongahela Incline funicular up to Grandview Ave. for great views of Pittsburgh. Walk over to the other funicular (the Duquesne Incline) on Grandview Ave. for a pleasant walk, while enjoying the delighful architecture of the Mount Washington neighborhood.
* Liberty Avenue is the home of Pittsburgh's Gay scene; true it's not anything close in ambience to the supposed Liberty Ave. from Queer As Folk (which is SO Toronto), there are few lounge/bars and dance clubs with generally unpretentious crowds.
Quick Tips:
Here's a tip for taking the "T" that was not mentioned in my guidebook or at the stop. Trolley fare from downtown to Station Square and points beyond is paid when you exit the trolley ( to Station Square; .60 to points beyond); however trolley fare is paid at the station when returning to downtown Pittsburgh.
Similarly, you pay the .85 round trip fare for the Monongahela incline at the top of the funicular ride.
The downtown is quieter than east coast US cities, but still retains some vitality even at night. I felt relatively safe walking alone both downtown and in the Strip area (possibly foolishly?)
Best Way To Get Around:
I did not bring a car and had a very pleasant visit. I enjoyed walking around in the downtown/Strip district and taking the "T" to get to Station Square/ Mount Washington/South Side area. Buses are available to get to the North Side, Oakland and Shadyside neighborhoods. I observed hailable taxis with relative frequency in the "Golden Triangle" (aka Downtown Pittsburgh) but not so much in the South Side neighborhood.
Some may prefer to rent a car for convenience, but as I mention, I did enjoy my trip without one. The bus and train stations are both located downtown in a safe-seeming area near some downtown hotels with plenty of taxi drivers waiting outside to have your business.