I am very organized. Unfortunately my DS is not. Jane and Keith and Betsy and I have discussed this, as evidently they share the same symbiotic relationship. The key, I think anyway, is to start somewhere (anywhere) in getting stuff in order and do not stop until that area is finished. Then move on to the next. Also be ruthless in throwing stuff away.
Tomovoz: First of all, I would mightily suggest a sleeper for your whole trip. The standard sleepers are not much more expensive than coach, plus you get free meals and, especially on the Coast Starlight, all the "perks" of the private cars, which, as I told you yesterday, are quite exquisite. Sadly, the Empire Builder (the main east-west line) is in pretty bad shape and does not have the "movie" car on the refurbished dining car that the Coast Starlight has.
On the west coast, I'd plan on stopping (after L.A., of course) at: San Francisco, Ashland, Salem (maybe--MB may have more to say, personally I don't think there's that much to see other than the Capitol), Portland, Seattle and Vancouver B.C. (if you're going that far north).