It's a crap shoot that time of year. The Siskiyous are the major obstacle, although Oregon can get some of the nastiest ice storms you'll ever want to see. The coast is generally clear although I encountered ice up the Oregon coast last January. Redding is kind of the point of no return, you can go west to the coast there if the mountains are blocked, although you'll also find some slick stuff on that route.
That's the worse case scenario, sometimes it's clear and beautiful the whole way. Keep your eye on the weather reports and 10 day outlooks.
Have you considered flying?
Just kidding, it's a beautiful drive after you clear Redding. The hills of S. Oregon are charming and the further north you go the better the mountain views.
Let us Northwesterners know when you're coming through and we'll have a get together.