Hi lincolnjkc,
I assume you are looking at the following
Hilton tokyo
Conrad
Hilton tokyo Bay
Hilton Odaiba
There are threads on the hilton forum for each hotel and I have stayed at 3 of them ( not the odaiba one)
Hilton tokyo bay is ideal for disneyland but a bit far for regular commuting into tokyo for sightseeing ( around 45-50mins each way just to Tokyo station then you have to get to your sightseeing spots) but is a good hotel. The travelling ( probably best to avoid rush hours if possible) may get tiring if doing it for a week
Hilton Tokyo is in Shinjuku (10min walk from Shinjuku station and has a bus shuttle running every 20mins or so at peak times and you can also walk in the underground passage ways form Shinjuju station) and has shinjuku nightlife , shinjuku goyen park , and the Metropolitan Govt building with the viewing decks and the shinjuku city park. The shinjuku nightlife is close to the east exit of the station ( the hilton is accessed via the west exit. Good transport links to temples and Shibuya ( for the scramble crossing)
Conrad- excellent hotel in Shimbashi ( the neighbourhood is relatively quiet at night but you are just south of Ginza with 2 beautiful gardens nearby and the line to Odaiba is practically outside the hotel. I would definitely consider it if you had lots of points or the prices are only slightly more than hilton tokyo. Bayside view rooms are wonderful, Excellent lounges ( can get busy at peak times). I would keep checking the prices as occasional flash sales occur which can make the Conrad more affordable.
Hilton Odaiba- On odaiba with views across to the Rainbow bridge , tokyo tower and you have odaiba to explore with shopping centres, parks and museums ( and a replica Statue of Liberty). there are 2 line into tokyo which can take a little while
As a Diamond you should get lounge access.
September may well be hot ,humid and wet in Tokyo ( with potential for the rare typhoon)
I would be tempted to split the stay with the Hilton Tokyo and the Conrad with Odaiba as a potential option . If you wanted to see disneyland ( and Disneysea which is unique) then I would consider Hilton tokyo bay ( around 1 hr by limosine bus from Narita airport)
I would also take into account your departure/arrival airport as it can take a while to get to the airport ( especially Narita with a very early morning flight- taxis are very expensive to Narita)
There are lots of good tips in the Japan forum and I found this site useful
https://www.japan-guide.com/
Regards
TBS