Hey look at that, another Winnipeger. Winnipeg, as well as the other small prairie cities I'd imagine, also have the disadvantage of just not that much competition and not that much in terms of newer rentals. When I moved to Vancouver 6 years ago, I doubled my salary from ~42k to ~80k. Most of the well paying jobs from that time were for Java devs at the big 3 or 4 insurance companies. If I wanted to work there, there weren't really many nice apartments nearby. Some were built way out in burbs, and now there's a few downtown and in Osbourne, but it's slow going.

Canadian software engineering salaries are bizarre though. I was making more in Africa than the average SDE in Vancouver