I'm not sure how much the city itself matters. I've shared this thought before. During the off season they'll live where they want to live regardless of who they play for. During the season they're gone half the time and the other half they're at the stadium or sleeping. They won't pick one team because of a bar or nightclub they like. I believe there's very few actual "all things being equal" choices faced by these guys. There's always going to be some factor between organizations outside of their geography. The manager, the coaches, the contracts, who else is on the team to compete for time with, the org as a whole....
I'd be curious to know how many established MLB players live in the same city/area in the off season that they play in.