One challenge of this is where to keep the minivan during the trip. It would be helpful if any of our friends in the Bay Area have a place where we could park the van with them during our trip. While we need to start at Emeryville, it's okay to stash the car in the South Bay if possible, as long as whoever is willing to keep it for me can shuttle us back and forth to San Jose's Amtrak station. (We're planning spending the previous night at the Hilton Garden Inn where I can use some Hilton points I have before they expire, so we'd probably go first to the hotel, unload our stuff, and then Lisa would stay in the hotel while I take the van to where it will be stored and then take the Capitol back to Oakland if necessary. I've stored the van at the Fremont station in the past, but Lisa is concerned about leaving the van there for three weeks.)
Where things get strange is in my attempting to use my Amtrak Guest Rewards (AGR) points. I have quite a few of them that we've accumulated through years of travel and using my Amtrak-branded credit card, although not enough to make the entire loop. The oddest part of working out points usage is on the NOL-LAX (Sunset Limited) leg of the trip. Now AGR points generally convert to money toward a fare at $0.027 per point, and that shows up pretty consistently on the other legs of the trip. On the NOL-LAX leg, however, it somehow drops to a mere $0.009 per point, which is absurd. What's even more absurd is that if instead of booking the trip straight through, you tell it to go from New Orleans to San Antonio to Los Angeles, the conversion goes back to $0.027 per point — but this is the same train, with the only difference being that it collects a sleeper and coach off of the Texas Eagle at San Antonio. (This is how we came back from the last Chicago Worldcon.) I suspect it might mean they'd require us to switch from one sleeping car to another in order to do this. Even more strange is that the cash fare for the NOL-SAS-LAX trip is $200 more than the NOL-LAX direct trip on the exact same train, but if you use points, it costs 150,000 points less!
I expect that the NOL-LAX leg is the one that we'll buy, while using points for the other legs of the trip, so this points pricing anomaly doesn't affect us, but it's still quite puzzling.
Once we are able to book our Worldcon hotel stay, we can start booking train trips. There are other things we may have to consider, such as the fact that we're setting ourselves to drive over the Sierra Nevada twice in winter.