Why not? In my experience (or more precisely, my wife's experience), she has gotten almost as many upgrades this year as I have as a Diamond. The reality is that many of us who routinely travel and stay in hotels have grown accustomed to asking for upgrades when they are not automatically bestowed upon us. There is nothing wrong with asking and in hotel parlance it is a common occurrence. It really has nothing to do with whether or not Hilton values you as a Gold, sometimes the property just doesn't upgrade freely unless they are asked.