Gaylene, so interesting! You are so right about the visibility here. Sadly, as you probably heard, the teen who was hit at a crosswalk on Monday in Saanich (not too far from where I live) has since died. That shows you just how poor visibility can be. It's quite shocking to me. It's not that there are no lights (although there are very few lights in my area, as it happens). It is more that there are many obstructions and there is a lot of glare from the rain. And it seems to get dark so much earlier than in the east. Actually, it doesn't "seem" to get darker faster -- it does get darker faster! That would be different for you, coming from Edmonton. But Edmonton gets a lot of winter sun. So the darkness would be noticeable for you in a different way, I'll bet.
Anyway...it sounds like I may run cooler than you (or maybe wear fewer layers?) or maybe walk into the wind? I'm not unwilling to layer, though, so can consider something like your strategy with Helly Hansen. But when I walk at night right now, I'm wearing a merino base layer, often a merino second layer, boots, merino hat, gloves, and my Lole puffer, meant for genuine cold weather! And oh yeah, a scarf!! And my reflectors, of course.
In the daytime I can get away with less and do. And of course on the rainy days, I need raingear, not a puffer.
I am not surprised by the rain=warmer and sun=cooler -- that's a Maritime thing and it was the same in Kingston (near Lake Ontario). The changes here are less extreme and abrupt (as a rule) and of course there is far more rain -- especially this year. OY!!!