I cannot stress the awesomeness of expensive winter riding boots. As I aged I've gone from running shoes all winter, to needing 300$ winter boots. I've spent the better part of the last 20 years riding outside, my circulation has changed over time, and not for the better...happens to us all. I too have three differing balaclavas, and the layering changes with about every 5 degrees in temp difference. Go out and explore in the chilly as it gets cold , you'll be able to figure it out, I use snowboard gloves in the real cold, but I can layer to about -40C. Wind proof above all else, from head to toe.