Sounds very grim. I live in a snowy part of Europe and very little of this applies, except the stay dry and warm part. Here are 2 things I learned:

1. Do what everyone else does, when they do it. And don't, when they don't. You could die.

There is usually a reason even if you don't understand it right now. You don't want to find out why when you're out in the cold and freezing.

2. Buy gear locally.

There's sometimes reason a certain item is on the shelf and not the stylish one from California, or the super heavy-duty one from Norway. Unfortunately, often this is only obvious in hindsight. Does not depend on price, but it does apply across the board from clothing to cars.