1. I 'toured' during full winter conditions. I have to say that midweight wool longjohns and top or Woolpower onesie are just enough of layers for me when riding. Top it off with Goretex bibs and a jacket and I am all set for layers on the body. I carry 3 pairs of gloves as you never know when You reall NEED a dry, warm pair when you're out there. You certainly need a pair for sleeping and perhaps a pair for riding. I use bar mitts/pogies so sometimes there is no need for gloves. it is wind resistance that matters more I think. There were times when I used to wear a ski helmet (we are talking in sub zero F weather) but for the past few years I am good with regular helmet and a balaclava. I would recommend ski goggles for when it really catches you during a ride and it is blowing chunks.
Winter riding basically means you ride until you can't. It's cold in the tent so you will be spending warm time in the sleeping bag (quilt won't do IMHO). You ride until it is time to find camp and then it's a quick succession of coordinated steps :-) Pitch your shelter first, cook next, boil water for nalgene and stick it into your sleeping bag. Undress quickly everything and slip into wool underwear, dry balaclava or a dry hat and jump into your sleeping bag that was warmed up by the bottle. Eat, perhaps cook some more (hot chocolate) and sleep.
I carry foam mattress and inflatable. Put your damp clothes between the two. Your body heat will warm up the inflatable mattress and help somewhat (no miracles) to dry your riding clothes and keep them relatively warm for the next morning (that includes your socks). I put my shoes in a bag to use as a pillow. That also keeps them from freezing somewhat.
In the morning it is about boiling water for breakfast or eating food that works against freezing (crackers etc...) - so my next recommendation would be to have a tent that works well for cooking while in the sleeping bag (and not dying from oxygen deprivation or setting the tent on fire)
The challenge in winter is about continuous management of condensation that could freeze so getting a sleeping bag that is very well insulated from getting damp from body perspiration is as important as getting one that won't let any draft in (hence my objection to a quilt)
Double wall tent is warmer. Tent less mesh netting is better as you want to eliminate cold wind making your sleeping quarters cold. If I am really sure
Stopping every few days in a warm place where you can dry your stuff may just be essential.
Winter means different things to people. People in southern US states talk about cycling in the winter, people in England talk about cycling in the winter and so do people in Finland or Maine or Alaska - winter is not the same thing in each of these localities.
