Although I live in Virginia Beach, I grew up in northern West Virginia about an hour from Pittsburgh. I think this is a very underrated city for several reasons. First, there are a lot of great restaurants in the city. Places like Primanti Brothers and Penn Avenue Fish Company are staples.
Second, this is a great housing market. Almost everyone lives in the outskirts of Pittsburgh. The housing prices are considered to be below the national average. When the economy took a dive in 2008 and on Pittsburgh was the only area where house values went up.
It's home to a great airport. Not only is it large with plenty of shops and restaurants inside, but it's easy to navigate and not usually slammed. I love flying here.
Finally, who wouldn't love spending an afternoon sitting at PNC Park watching a Pirates game? It's just relaxing and fun.