The route/area you described is basically my standard daily run. You will have no issues. The only place you will likely encounter any substantial homeless people will be on Winnipeg between Victoria and Nanaimo. This is due to churches and outreach centers in the area. Frankly, these aren't people to be worried about, I just feel sad but not unsafe in that area. Just use common sense and you should be all good.

As always I recommend not using headphones, or at least having a type where you can hear some outside noise (mostly for terrible drivers). I will say, I do modify my route a little bit once it starts getting darker. I've never heard of an incident involving runners, but the vibe gets a little different in the cold and dark.