I recently got a Citi Prestige card (note lack of referral link!) and I'm in the middle of trying to book a 5 night stay in Tokyo to take advantage of the 4th night free benefit.
The thing is you have to book through the Citi Prestige concierge at 1-561-922-0158
So I found a hotel I wanted. https://www.booking.com/hotel/jp/super-hotel-lohas-akasaka.html
Then I called the number but she could not find the hotel. Turns out she's looking at the hotel's website here: http://www.superhoteljapan.com/en/s-hotels/akasaka/
And when she goes to the booking link, this hotel isn't on the list of available hotels on the English page. If you go to the Japanese page and have it translated it shows up but since neither of us read Japanese, she could not go ahead with booking this hotel.
I had already made a reservation using my dates just to hold a room so I have a backup.
Then I found this hotel which was showing up on the Super Hotels' English website:
So today, I called the concierge again to try to book this hotel. And while she was able to find the hotel, it required her to create an account to be able to book a room so she said she'll send this to one of her colleagues who speaks Japanese to call them overnight and try to book the room and get back to me by tomorrow.
So the catch is there is only one room type I want that is available on my dates, so I cancelled the reservation about 10 minutes before I made the call but now I'm left with someone potentially taking my room before the concierge is able to call and book the room. Well, in my favor, it's middle of the night in Japan but then again the US is wide awake at this hour. So I'll just not make another booking and just hope that the room is still available by the time the concierge makes the call.
All in all, this is not really a smooth process, if the hotel is a local brand overseas and doesn't have a good website. If it was a chain hotel like Marriott or Hilton, this should be very smooth I'd imagine. I'll update if the reservation runs into further issues.