[Azathoth]

Literally the best investment in gear I made was a pair of quality long johns (arc'teryx), tied or second would be the sealskinz socks,

Add Micro Fleece tops.

Their is a an alternative to Gore, I can't remember the trade name but it's a silicon based product out of Japan which is suppose to be far superior, and then eVENT made by some other company, I believe GE which is comparable.

What size are you? I have a gore hardshell that i got that is FAR too big for me that I would like to trim out of my closet to fit more arc'teryx stuff.

If you are layering up a lot, even with GORE products on you will need a layer with a pit zip. GORE is breathable but it's not THAT breathable.

We had some really bad (read good) winter weather in our area 2-3 years ago and running so playing outside in January in -20 to -30 was possible. My layering system was

-Base Layer IE Long john stop / wicking layer
-Mid weight layer
-Softshell - can be the GORE layer depending on if it's wet and cold, or dry and cold. With these 3 layers on and standing still you should just start to feel cold
-Moisture layer, your GORE, eVENT layer, can sometimes be merged in with the 3rd layer depending on the conditions. Something to consider is the durability and ruggedness of your clothing. You don't want to wreck your nice GORE jacket by snagging it on something