So we went to a travel agent in Portland who specializes in travel to Japan. She's Japanese herself, too, which we figured would help in case we hit some block we've missed due to cultural blindness. We explained what we wanted, giving a range of dates on which we can leave Osaka, and that we'd prefer the Royal Suite if they can get it, or the next-largest suite after that, or any of the "A" suites, but we'd rather not travel in the tiny "B" suites.
There are a fair number of overnight sleeping trains in Japan, but booking them seems nearly impossible, as opposed to merely difficult the way it was to book the ScotRail sleeper from Glasgow to London in 2005. It appears that you can't book a sleeping compartment until 30 days before travel. Really? You can book a sleeping car on Amtrak nearly a year ahead of time, and in fact it's a good idea to do so because they sell out early. Even the ScotRail sleepers appear to be running around 90 days in advance.
Next barrier: You can't book by phone or internet. You have to go to a JR booking office and do it in person. You can't make the reservation from outside of Japan. The travel agent has to hire someone in Japan to go make the reservation for us.
Next barrier: You apparently can't make the reservation for a sleeping compartment as a supplement to a JR rail pass unless you already have the pass issued. But you can't get the pass until you get to the country, because what you buy in advance (and for which we've paid but not yet received) is an "Exchange Order" that we will exchange for the actual passes when we get to Narita. This means that even if the person sent down to stand in line at the JR office can get the reservation, you have to pay the full price, including the rail transportation, even though by the time you get there to use the reservation, you'll have the pass.
At least in 2005 we were able (by phoning; it couldn't be done over the internet) to book a sleeper on ScotRail without having the pass yet. They understood that I was only paying for the sleeper supplement, and that I'd show our rail passes when we claimed our room in Glasgow. (And aside from the room being fiendishly overheated and there no way to cool it down, this worked fine.)
Finally, while everything I've found on-line seems to say the sleeper charge is a flat rate regardless of whether one or two people are traveling, our agent says it's a per-person charge. Now, personally, it seems to me that the agent's people in Japan are probably overcharging this way and pocketing the difference as their commission. But if they'd just come out and say so, I'd feel better.
We bit the bullet and told them to go ahead and try to make the booking anyway. But instead of paying around $500, it's probably going to be closer to $1700 if it happens in the best-case scenario. (It will cost less if they can't get the Royal and we go down to a smaller compartment.) That's painful. I keep telling myself, "It's a once-in-a-lifetime opportunity," but it still hurts.
We won't know if we got anything until around August 10-12, and since a bunch of other plans have to be worked around that trip, it leaves about four days of the trip in limbo. I don't like leaving things unplanned.
We're also thinking of taking a sleeper from Saporro back to Tokyo, but in that case, we're going to take a chance on a compartment of any sort being available for September 13 or 14 when we get our JR passes on August 28. In this case, we should able to actually use our rail passes and only pay the sleeper surcharge.
If we can't get the overnight train, we'll have to take an extra hotel night somewhere and travel during the day. I'm sure we'll manage, but I hate leaving loose ends in my planning.