I- Fly Pittsburgh to Tampa or Orlando and drive toward Ocala to play the following - World Woods Pine Barrens and Rolling Oaks, El Diablo, Brooksville CC, Golden Hills. If you are able to access them, add Black Diamond Ranch's Quarry, Southern Hills Plantation, and Golden Ocala.
DOWNSIDE - Hot and not very good nightlife options once you are done with golf
PLUSSES - Great daily-fee golf, very inexpensive, and won't be too crowded
II- Fly to Minneapolis/St. Paul and get a minivan and drive 3-4 hours north to play Brauer's courses north of Duluth. The Quarry is supposed to be his best course. If you can get on, add Northland to the trip. Off the radar, try Cloquet.
DOWNSIDE - Might be hard to get to and only offers some casino action for fun
PLUSSES - You'll be the first to play these amongst your friends
III - Head to Charleston as previously mentioned. Some great golf there.
IV - Baltimore for Bulle Rock (just had the ladies), Beechtree (before it closes), and Mount Pleasant (seriously, this municipal has a great set of 4s).
DOWNSIDE - None
PLUSSES - Close to Pittsburgh, all daily-fee, Beechtree is pretty reasonable
Have fun whatever you choose