I was in town for a job interview (in Moon Township) and decided to venture into the city the evening before. Here's the run-down based on this one visit:
Food: I was half (or more) starved by the time I got there. I ordered the veggie chili and it was quite tasty and the Philly Cheesesteak. The cheesesteak was "hearty" and quite generous but given the size (and calories) I doubt I'd order it again. I ended up taking it back to the hotel (for what I thought would have been a midnight snack but did not happen). If I happened to be in the area and in the mood for a cheesesteak, I'd head back; otherwise I'd not bother.
Service: It was "blah.". I could tell my waitress had a rough day and it was a bit crowded that evening (a Monday night) but she just didn't seem all that friendly (perhaps at least she could have faked it I suppose).
Parking: I live in the Los Angeles area where parking issues are a way of life but Shadyside parking is unbelievably complicated. (or I just don't know the insider tricks just yet) Unless I lived in the area or there was relatively easy public transport to this otherwise very charming neighborhood, I'd never recommend heading there for a simple meal.