If it's "Down in New Orleans", or " Meeting in St. Louis", or " Dreaming in Galveston" , it seems to me Americans want to be somewhere they aren't. If it's " Vagabond Shoes in New York" or. "Flowers in the Hair in San Francisco" it seems to me they are looking for change of life style. They are not sure where they are going but they want to know " The Way to San Jose " without much idea of what they will do when they get there.
Having said all that, maybe we Canadians are a charmless bunch without finer feelings about our cities in song, or maybe it's just me that is charmless . Certainly the Irish and Scots are also full of musical blather about their bays and Islands and their songs are both evocative and passionate. Or, maybe we see our cities as not needing promotion, or it's the job of the Board of Trade and we are for " peace, order and good government." At least our constitution says so. We live in a country that has the largest land mass in the world and there is only 32 million or so, of us to manage it. We are blest with a life of cities that are safe and sound. Why would we continually brag about them when much of the world is enduring the conniptions they are enduring. It isn't kind to brag about your good luck. Maybe kindness is a substitute for charm.