I am planning on going. Weather will be the factor. I have some Les Schwab super easy (I haven't tried them out) chains for the Tomato, but none for The Pointy Trailer so I want bare pavement. Please let the Siskiyou Weather Controllers know that. Then I think all I have to worry about is my road.
They usually sand Siskiyou Summit pretty good. Usually. If it's snowing between the summit and Yreka and they're throwing chains for Politician Hill you can duck off the freeway at the bottom by the rest area, drive down the river a ways and come into Yreka that way.
How 'bout cutting over to 101 somewhere in Oregon and just riding that all the way down?