Well, I def don't want to hijack this thread, but the OP and I are doing lots of the same stuff! Long story short, I hated rescheduling from April to June b/c it's going to be just lovely weather in April and I know June is iffy. kbmartin, I'm jealous! But at least we leave by mid-June b/c the ticket prices sort of forced me into not staying too late! Flights departing Japan after 6/16 were too much pricer vs. our original tix for me to justify (b/c of airline hub shuffling or the Olympics nearing, idk.) So as much as I hate the shortness of our trip, at least we aren't staying into the worst of summer. It'll be worse when we arrive back in the US probably, but at least then I can hole up in the A/C w/o missing anything. Maybe I'll even sit under a fan and write a trip report.
As for the Hilton -- well, I haven't yet decided on our TDR area hotel, so we might end up in the Hilton Tokyo Bay. That plus Port Vita near USJ will mean 5 nights of "nice" semi-western style hotels, and probably 5 nights of sleeping in Western beds.
So for our 2 Tokyo nights I'm leaning toward something like the Dormy Inn Express in Asakusa (DD thinks late night "free" ramen is a selling point, and they at least have a decent bath area, though iirc they don't have true Japanese-style rooms, just sort of Western-Japanese rooms or Western). Or Andon Ryokan (I love the story behind it, but it's going to be all gaijin). Or Edo Sakura (horrid no cancel policy and a bit more than I really want to pay esp. without cancellation options -- but gorgeous tatami rooms AND daily tea ceremony.) Also considering Onyado Nono Asakusa and Family Inn Saiko in Toshima, etc.
So, I don't think OP and I are looking for the same thing in our Tokyo hotel. I don't have height to worry about bed-wise, and my #1 wish is Japanese style bedding and hopefully nice smelling tatami mats

-- possibly some tiny bit of Japanese cultural activity such as the tea ceremony convenient in house. Maybe an onsen/sento. The bath would be 100% required if it was just me, but for this rushed mother-daughter trip that's not priority b/c DD might not want to do that anyhow.
Ah, OP, if you love carousels (hey, some Disney peeps do!) one other thing we might add to our trip, if I can squeeze it in, is a couple hours just to visit a small old-style amusement park in Toshima that has an incredible 3 ring carousel built in Germany and used in Coney Island for years. The rest of the park, based on its website, reminds me of some of our old US historic amusement parks, but we'd just be paying the $10 or so each to go in just to see the carousel El Dorado and then another $3 each to ride it. As a bonus, the train going out to that area is a neat design. But that's all we'd do out in Toshima. Then we'd go back to Shibuya/Shinjuku/Ikebukuro shopping or whatever. Yes, we're going to Japan for amusement parks lol. It's going to be way too short a trip.