I used to courier luggages between locations. Very efficient and reliable. However, I am not sure that that accept foldable wheelchairs. If yes, that would be great.

I think you have to do it over the counter. My friend told me that telephone reservation is possible but you may need to speak in Japanese.

I had experience about bringing smart drive with JAL. I encountered no difficulty when taking international flight with smart drive. However, when taking domestic flight, the airport / airline staff spent a lot of time to research for info (even I had all written documents) and “seek for approval”. Allow extra extra time for checking in.

I will suggest you courier your luggage, then you only take handcarry size bag to bring”just enough stuff” for 1 or 2 nights. Normally, you expect “next day arrival” of your luggage. Remember to check the cut-off time with hotel staff.

May I know are you referring to Hilton in Shinjuku?