Originally Posted by gengo

It looks like there are no Park Suites available for my date blocks. If I check individual dates, there are some available, but not for any block I could come up with, so I would right that off as "not happening".

Most of the time I love upgrades, but I always try to book the room I am comfortable booking and view any upgrade as a bonus.

ETA: Wait, I just checked, and if I split my nights 3/3/3 (instead of 5/4 or 6/3), there is a Park Suite King available for the middle three. I really would rather do just two different hotels, but I would consider a 3/3/3 split if it was nearly a sure thing to be upgraded to the Park Suite King. Is anyone willing to share a contact email address for someone in the hotel who could better answer this? I have reached out to GMs before trips to ask clarifying questions with both Hilton and Marriott properties.

Also, Conrad Tokyo became available again for the first block of 5 nights and I am now strongly considering that for my first block and moving to one of the other options for my second/last block of 4 nights.

For the Conrad Tokyo, I would be booking the King Suite Bay View. For 10,000 Yen more, I could book the King Executive Suite Bay View - looks to be the exact same room/room size, but grants access to the Executive Lounge.

However, since I am Hilton Diamond, I would automatically have access to this lounge at this property, right?