Thanks for the tips!
I have a hammock, though I've yet to do more than nap in it. Might be worth a try. I've been thinking about converting a woobie into an underquilt.
That roll mat I used underneath a Klymit Insulated Static V Sleeping Pad. I also have a self inflating pad and a egg-caryoon style inflatable but those seem more for summer.
I think my tent isn't ideal for many reasons. I was thinking of getting a new one, but I'm also aware of that 'just one more piece of gear' mentality.

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