In general write a list of 2 or 3 places that look sick to you and visit.
Because of skating and friends from college I've couch surfed all up and down the east but I've only lived in New York City and the Carolinas. They're polar opposites in a good way: Shit winters vs shit summers, party going art scene vs. art communities more into craftsmanship, good pizza vs good barbecue, blah blah.
I will recommend checking out Atlanta. It is affordable for what it offers: big city life, a lot of single women, good food, good skate scene. The biggest negative is it probably has the 3rd or 4th worst rush hour traffic in the North America.