don't know if Joni Mitchell still qualifies as Canadian but several of her songs would seem to be appropriate from any or all of the perspectives you mentioned.

Leonard Cohen is a bit trickier, but "Bird On a Wire" comes to mind.

In the midst of my own music fog I am at present blanking on a number of Canadian "roots" singer/songwriters that I have come across on "Music Fog" over the past several years - and of course can not recall any of them for now. Unfortunately, I tend to pay much more attention to the song than to who does it or where they are from these days - so not much help. But would love to listen in on your series. Will it be streamed or available for podcast on-line? If so, please give links and dates if not available for later podcasts.