I'm mostly concerned about down-time/around camp and sleeping. I do alright while hiking, but I'm looking to better those layers with more synthetics and wool later on.

For sleeping and around camp (hiking, too, if needed) I just got a fleece balaclava sort of hat for $3! Soft and stretchy.

Lots of good thoughts in the replies so far - much to consider.
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Why am I online instead of hiking?