A bit over 23 miles this week. I try to average around 20 miles/week or around 1k/yr. I'm actually a little shy and will have to push my numbers up a bit to make it this year!
I ran with a local store for a few years as part of marathon training. During that ramp up of my running I learned to run in just about anything. I've run in single digit temps, snow, lightening, dark... Just about everything :)
There's always an excuse to not run, getting through those excuses is the trick.
Once, our running group (there was only a handful of us) helped a car get up a hill. It was stuck in the snow haha.
With the cold, you've gotta just keep running from summer, through fall into winter and you acclimate with the weather. I never really experience any breathing issues in the cold. once it gets down below 20°f I start putting aquaphor on any exposed skin (cheeks/lips/nose).
I don't generally run "at night" but as winter hits, I run in the dark for sure. Lots of lights, including a head lamp. I actually feel more visible to cars running at night, but generally it's associated with winter and colder temps too.
I have never really had issues with "red 11" (aka nipple issues) running, and also quite enjoy running in the rain. A light rain can be a quite enjoyable.
I've run in Toronto (Brampton area) before. I've been up there for work a few times. Looking on Garmin connect, seems it was back in 2017 :)