Yikes! That is a challenge, Mike. I fly plenty and see you guys out there in all kinds of crappy weather, and I completely sympathize. Youre working hard for 30 minutes in one stretch, and then standing around while the wind is freezing a plumbers behind for the next 30 minutes.
So I dont think any single piece will do it. Id layer up. Start with a very light layer that wicks moisture and offers some thermal assistance. Patagonias Capilene 1 is ideal for this ($38 for long-sleeve tee). Over that, wear something warmer and woollier. Throw on an Icebreaker Mondo Zip ($70), a mid-weight layer that really packs a lot of thermal agility. When youre working hard, it breathes. When you arent, it holds warm air close to the skin.
Tricky part is: what next? My vote is for an REI One Jacket ($190). This is a soft shella piece that has some insulation, is nearly windproof, and easily shrugs off light rain and snow. So its great for those stop/start kind of days. You might think, at first look, its too light. But its a very impressive piece. Tough as hell, too. More reassuring visually is L.L. Beans Noreaster Commuter Coat ($200), a longer piece than the One, with Gore-Tex and Thinsulate insulation, but one that, in my opinion, doesnt offer the same agility and flexibility as the One.
All of the above have complementary pants, usually for a bit less than the top or jacket.
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