Look up "St John's Waltz" by Ron Hynes. It doesn't meet any of your listed criteria, but it's a brilliant portrait of the character of what may be the oldest continually inhabited city in North America, long as you consider Newfoundland part of North America. (St John's is perpetually feuding with Quebec City for this title; far as I know no American settlement has a decent claim.)

For a song about no particular city but which does meet your theme interests, look up "Paint Me a Picture" by David Essig. http://www.davidessig.com/rchg.html