BTW, one thing I forgot to look up. Southwest will be happy to fly you from Oakland to Portland 6 times a day. Their standard "flexible" fare is $297 one way, with "Business Select" (mainly, you get on first) at $313. Restricted fares range from $79 for the first flight of the day to $145 for most of the others. Southwest seats have better pitch and space than most cheapo airlines, but they aren't even close in comfort to the worst seats on Amtrak; OTOH, you only have to sit in them for an hour or so on the OAK-PDX run. Looking at Southwest because they're average-priced, and unlike other airlines (but like Amtrak) they do allow some checked baggage for free.

So comparing Southwest's standard fare to a roomette on the Starlate (which actually has been near schedule most of the time recently), sleeping room & board on the train only costs you $105 extra, which doesn't sound very bad at all.