Originally Posted by gdl203
Sounds like you're a consultant who spends the week on assignment at clients' locations. If that's the case, the most important question is what do you like to do on weekends - since that's the only time you'll spend in your "home" town. That should help you narrow down choices pretty quick. Do you like to party til the morning or do you like to hike or ski, or do you like to eat out and go to the theater, etc.. ?
Also, are you free to spend your weekend wherever or do you have to take it home? Since you are unattached, you could ski one weekend, go windsurfing the next, and then sit at home for the third.
If you plan to do that, either find somewhere with a low cost of living where you can get a decent 1BR for little $$ since you won't be there often or find yourself a roommate and go for something like chicago for the convenient flights to client and travel locations (and the roommate will make sure the place doesn't fall apart when you don't come home for 2-3 weeks)