Red Mountain pass into Silverton should be #1 on that list, easy.I’m giving it a shot this winter with the Falken wildpeaks. Ask me how it worked out next spring!
For reference I ski ~50 days up the #2 sketchiest road.
(It’s not actually that sketchy 99% of the time, but it was funny to see it in an article)
Get thyself some dedicated snow tires. The difference is large on stopping power and traction.