Cobalt,
do you need to actually live in a city in order to work?
Do you intend to bike to work, or use mass transit to commute?
Are you going to retire soon, or not for many years yet?
Do you intend to drive out of the city in order to go on bike rides, or are you wanting to ride from home?
These questions and more will have a big bearing on your decision.
You might want to consider factors like mass transit and gas prices/availability when thinking about all this. Right now, suburbs are rapidly going down in value because people no longer want to drive a lot to get back and forth to work, plus they can no longer afford a large house and high mortgage. Smaller urban dwellings are now becoming more sought after.
Just a few things to think about.