I took the jump last winter and bought the Fasterkat cycling boots. I haven't yet ridden below 25F but they are very comfortable there and I am a long limbed 62 yo who has always had cold feet and hands and is now finding that getting worse. The Fasterkats are ~$200, so not cheap and they aren't shoes you want for the non-cycling part of our day, but they are very walkable as well as excellent riding shoes (SPD/2 bolt compatible). Also good footing in snow. (Just checked that out last week.) They are the best winter cycling shoe/boot I have ever used by a lot. And they are only the #2 boot from that company, advertised as good to 25F. #1 is 10F or colder. Just not necessary in Portland, OR.

Ben