I'm lousy at the search function, but somewhere either in the touring subforum or in this one about two years ago a person from Arizona (I think) created an entertaining thread about his adventures riding an ordinary (high-wheeler) from S.F. to somewhere in AK. He was re-creating a famous trip from a century ago. He had an extended stay in Eugene to rebuild his wheel, but I managed to miss him. If you can find his thread, then you'll have a good start.
If you want to go south to north on the coast, you have two choices. You can have mostly dry weather and head winds by traveling between May and October. Or, you can have lots of rain and tail winds by traveling during the other months. Pick your poison. Winds have more variability inland, but the overall pattern is much the same.
Sounds like a fun and challenging trip. Have fun and let us know how it goes.