Forget about getting an upgrade at the NYC Hilton.
I recently complained that I never seem to get ANY recognition at that property, despite the fact that I love its location and frequent them whenever I'm in town.
While I would recommend the property just for the location, despite the fact that their treatment of Diamonds is not that great. They don't give you anything special except for access to the 44th Floor Lounge. They get too many Diamonds staying there to treat anybody special.
They typically have about 150 rooms (floors 34, 35 and 36) set aside for Diamond members, but these are the standard small ones -- nothing different except for free bottles of water and robes, and once in a great while maybe they'll give you a better room on the 43rd or 44th (so I've heard, although I've never gotten one in many stays). Be sure to check in on the Lounge on 44 or you won't get anything at all! The front desk staff in the lobby doesn't even have permission to give you these rooms.
The bottom line if you are looking for extras is stay elsewhere!
At the Waldorf is another story. I have not had too many stays there, but when I have I've gotten large suites! Old hotel, but large rooms that were impressive. ^