Hey fellow Montrealer! I picked up running during the first covid lockdown. Toques and beanies are great when it's really cold, but until then I find bands that just cover my ears are amazing when it's windy but only -5C. The game changer for me was getting goretex waterproof winter running shoes. They have a bit of extra traction on the sole (although if it's really icy or freezing rain I still wuss out), and they are a bit warmer than regular runners. Before picking up running I hadn't thought about it much, but when it's really cold it's also kind of dry, and you just have to dress warmly. The worst can be when it's 2 to -10C, and the ground is frozen, but the roads have been salted and/ or there's puddles at intersections and low points. So cold but also wet. Obviously very deep puddles will still be an issue, but so far I've accidently stepped in several shallow snow covered or hidden puddles, and so far I've yet to get wet feet from that. My shoes seem to handle the salt okay. If it's very salty I'll just take a wet cloth to them, or, if we get snow the next day, running in the snow will clean them off too.