I put neoprene covers on my mtb shoes (I don't use road bike shoes, since I get off and walk around now and again) and found that the pedals are a major heat sink. So, I found a cheap online source of those adhesive foot warmers which I put under the insoles of the shoes. With rain pants over polyester sweat pants over a thermal base layer below, and a rain jacket over a long jersey over a thermal base above, and a pair of arm warmers, a balaclava and ski goggles, I was good down to the high 30s, as long as I remebered to unzip and zip going up and down hills. As noted in your treatise on cold weather, managing moisture is the important thing. Also, how you feel when you step outside is not a good gauge of how things will feel after the first mile.
Some of the retailers are discounting winter gear already and I got a pretty good deal on a thermal jacket that should arrive this weekend for temperatures in the 20s and 30s. The roads are dry here, so barring any problems with bad plowing or salt, I'm looking forward to getting in a few dozen miles. I ride 700x28 gatorskins which are relatively slick, but I'm about one bike expenditure away from being single again. The studded tires sound interesting, thought. Decisions, decisions... I'll keep to the dry roads with wide shoulders; although I have noticed that cold weather Sunday traffic is pretty light on the back roads.
In other news, a 2004ish Trek 3700 mountain bike in bad condition found its way to me some months back, and I've gotten it to be rideable. While not a fat tire bike, it's the first mountain bike I've ridden and, dang, I took it out for a spin through a snowy field two weeks back and had a blast wearing ski pants taped up to stay out of the crank, boots on platform pedals and a ski jacket. I took along a backpack and made a grocery run out of it.