As far as the warmth thing goes, I have ridden in temps sub 20s and here's my secret......I wear a wicking layer right next to my skin. The best thing I have found for that layer is some wicking thermal underwear from LL Bean. Over that I add only one layer of the warm fuzzy stuff, and then I put on booties and a wind-breaker jacket. The windbreaker is key for me. It keeps the wind off, which is the cold part to me, and allows me to unzip to get circulation. Other than that I just expect the first sweat. Once that's initial sweat is over I usually regulate. Be sure to wear tops with zippers so that you can unzip even centimeters. Believe me, exposing a centimeter of skin around my neck sometimes is all I need.

Just my two cents