afang:
As a HH Gold, 1 am batting about .200 on getting an upgraded room @ New York Hilton. And that usually involves a polite request at check-in.
As a HH Silver, I believe your chances are somewhere between slim and none.
Frankly, I am happy simply with access to the Exec Lounge for a quick, fruity breakfast and speedy check-out.
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He who dies with the most miles ... is dead.