Somehow never saw this thread before now ....

And to go back to its origin: the person that started it lived, and perhaps still does live, in Windsor, Ontario - perhaps he didn't spend his formative years there, and perhaps he lived out in the (rich) suburbs, but the idea of anyone in Windsor not getting this song is bewildering to me. I grew up there, about three blocks from the Chrysler plant, and even though we didn't have canals and crofts, when I first heard Dirty Old Town, I knew immediately what it was all about, and the images it evoked were from my own memory. What I find particularly ironic, is that the pub this person apparently played in regularly - the Kildare House - was right across the street from a foundry that was a vision of hell, in my younger days. We had to pass it walking to and from high school - behind a rusted chain-link fence, there were partial
walls and roofs of old sheet metal, big industrial ovens and boilers; heat, grit and smoke drifted out, and we could see dark, scowling men working, their sweaty bodies gleaming from the flames around them. Once in a while, a passing student would receive a burn from an airborne cinder. Like the warnings of some fire-and-brimstone preacher, it seemed to be there as a threat of what awaited if we didn't stay in school ....

All of which is to say, I suppose, that the OP's perception of Dirty Old Town says much more about him than about it.