OP here.
Thanks for all the advice, I'll continue to review the information.
I purchased some drop-bar bar-mitts and insulated waterproof shoe covers that extend up over the ankle. Also some lightweight wool glove liners. This weekend will be a bit warmer, though probably rainier, than last. My toes still feel a bit swollen. Overall between higher temps and better gear, it should be a better day.
Cheers