Player 1:
Something else that occurs to me is that we'll probably want sleeping furs before the seasons turn cold*. However, between hunting and tanning we should be able to produce those ourselves as long as we get SOME chance to work on it (a day or two would be enough, possibly when we're otherwise lounging around a town somewhere).
* I am assuming that the campaign will start in some other season, because picking midwinter as the perfect time to start venturing out would be silly.
Gear bonuses for Making Camp won't stack, it would be whichever gear gives the highest bonus that will be counted. But there can be other uses for different gear such as Flint & Steel if you want to start fires for reasons other than making a cosy camp fire.
For rolls to avoid getting Cold, then everyone will need appropriate clothing of course.
And, yeah, I'm not going to have you start out in the middle of winter, after all, that would be mean...
To make things easy, I'm thinking we will pick up on the first day of Summer.