Cities to me are like people. Each has a complex personality based on its history and geography. Some places take longer than others to "get" and I hate to leave until I do.
Butte, Montana really didn't gel for me until my second afternoon driving through a mostly vacant downtown, under a dense, relentless rain cloud. I stopped around the corner from an old, supposedly haunted brothel with a mannequin in the upstairs window, hit play on my stereo and the Drive By Truckers came on, singing "Where the Devil Don't Stay."
Butte is a manly, miner's town. It's all orange bricks and pot holed roads. There are casinos around nearly every corner. Just standing in the middle of it makes me crave a PBR.
I haven't been to Pittsburgh, yet, but I think it may feel similar.