I dropped from Diamond to silver last year as company no longer books Hilton. Now Blue
But moving up in the SPG ranks
I'll give you a bit of encouragement.
The difference between Hilton and Sheraton (in Sydney):
Last week I arrived at Hilton Sydney and checked in at 7pm.
Front desk: "Sir, you've been upgraded to an executive room"
Me: "Is it possible to get a relaxation room?"
Front desk: "Sorry sir, we are fully booked tonight".
Me: "But I can see availability online" (showed her on my iPhone).
Front desk: "Sorry sir, there is nothing I can do".
Arrived this morning at Sheraton Sydney and checked in at 11am.
Front desk: "Sir, you've been upgraded to a park view room".
Me: "Can you check if there are any suites available?"
Front desk: "It's a bit early but let me see what I can do... I can see one suite available but it still need to be cleaned. Do you mind waiting in the lounge and we will call you as soon as it's ready?"
Me: "No problem, thank you very much".
Front desk: "will you need late checkout tomorrow? I can do 4pm".