I'm in Maine too. Yesterday I rode to work in the morning and it was 33 degrees out. I wore synthetic base layer pants with shorts over them, wool socks, a merino wools base layer top, wool sweater, light wind jacket, light gloves, winter hat (the kind that fully covers the ears... it fit surprisingly well under my helmet).
I was plenty warm, even from the start. About 6 miles into the ride I was actually so hot I took off the hat and gloves.
I can't say enough good things about wool. It doesn't have to be cycling specific, you can get a thin merino wool sweater pretty cheap at thrift shops or TJ Maxx and wear any wool sweater over it.
So don't give up on your goal, you can ride comfortable in the cold.
Congrats on the first two goals