Kendall, I'm in the same boat as you, trying to figure out my extremities. I'll be going to Vermont, expecting temps around 0*F for most of the time, plus (or minus!) windchill…I'll be using 40below overboots, vb. socks and light trail runners for my feet.
I think you will be fine with most anything around 25-30*, at least for moving. your inov8's plus warm socks should e fine. But you will need to keep the system dry, or at least keep it from freezing at night.
Michael, good call on the subway bags. Two bags per day, plus one extra is three, get a free foot-long with each $5 bag…three footlongs per day…three meals per day…
I think i've got my menu worked out for the trip too!
just a thought, but if you wear vb. socks, then you don't need wp/b socks, just another waterproof layer as there shouldn't be any moisture inside it. could save some $ and just go liner-plastic bag-thick sock-plastic bag. Bring extras, but it should still be lighter than wp/b socks unless you're heading out for a long time.