Okay, so I've never been to Winnipeg, but this song has been playing on my Pandora station recently, and I really like it. I think "Winnipeg" can be whatever you want it to be, whatever you may choose to blame for having a less than stellar life. For me, "Winnipeg" would be "work". Really, we could all just enjoy life for what it is, but it's easier to blame other circumstances: the city you live in, your job, your relationship, what have you.
Other than that, I think the song is beautiful and bittersweet: