So here's a quick shot of my winter setup from the weekend before last.
My HH Explorer Deluxe is in the foreground, with the HHSS underneath, and the HH Hex tarp in skins above it. In the background is Weasel's HH Expedition with a WB BMJ tarp that he's deploying over that.
Weather got down to about 22F with 30-40mph gusts in the middle of the night the first night...25F with similar winds the second night.
Standard HHSS deployment with HHSS UC and OCF pad, along with a space blanket above the pad under the hammock. Inside was a synthetic 20deg bag with fleece liner and standard issue poncho liner.
Worked like a charm under these conditions.