So I finally pulled the trigger so I figured I'd fill you all in. I ended up buying a Browning Hells Canyon Parka. They were on Sierra Trading for $150 (normally $300) so I thought that was a good deal. It is a decent puffy on the inside and then a shell that zip together. I think this will do me ok for now and then in a couple years I can figure out what I need.
The day after I pulled the trigger I found a guy selling a bunch of filson gear on here, all in my size and while it killed me to spend that much money on stuff at once I knew is was going to be totally worth it so now I have the Browning Parka, a Tin Cloth Jacket, Tin Cloth Pants, Waterfowl Sweater and some other stuff so I think I'm set for a while as far as clothing goes now.
