I had a Homewood Suites proactively call me last week to tell me I was upgraded from a 1BR to a 2BR suite. Granted, I did put a request in the notes because I was with my wife and 2 girls. I doubt they were calling many Gold or General members that day with the same info. (BTW, this same Homewood has Diamond Parking).

I also frequent an Embassy where I get a high floor corner room away from the “atrium”. All rooms are the same in size, but I get the best room on property when I ask.

Sometimes it does take asking. But I rarely have to ask in Asia, as others mention. I’ve had some pretty amazing rooms over the years as a Diamond.