I grew up in the subtropics and live in So Cal., so I'm probably just as 'thin skinned' as you. Even so, 30F is not all that cold.
When you are at rest at night and early morning -- a base layer plus one lightweight insulation should be enough. You can add the Driduck jacket if the winds are howling.
When hiking, it may be cold the first 15 minutes -- so you can hike with base and driducks -- but after that, I am pretty sure you can shed the driducks.
For head and hands, fleece beenie and gloves are all that you'll need (bring them, even though you may not end up using them at all). I would leave the Goretex mittens, etc. at home.
Your second long sleeve MTS top and long underwear bottoms will be good for sleeping in, and the Wisp should keep you warm.