Aging and out-of-date infrastructure, no beltway, a complete lack of hustle, and a large geriatric population... not to sound like a debbie downer or anything
Definitely hit up Primanti's and Quaker Steak and Lube. The city looks beautiful at night, and PNC park is arguably the "best" ballpark in the nation - and because the team stinks, tickets are cheap!
If you're considering work here, I'm partial to the northern suburbs. All of us stuck up out-of-town-transplant Cranberrians find it haughty enough to survive amongst the yokels... er... yinzers. Just do what you can to stay away from needing to commute through a tunnel. Even with large "MAINTAIN SPEED" signs, people still can't figure them out. However, like Swacer mentioned, Pittsburgh is the worst city I've ever had to navigate. Aside from continuous construction, the street signage is horrible.
If you're here on a Friday night, you'll definitely want to head to Wexford for the Starlite car cruise. One of the largest, if not
the largest, weekly car cruise in the nation.
Oh, and in case you haven't yet caught on to my condescension, prepare your thick skin -- no one is afraid of hurting anyone's feelings