Well, based on my experience, I would say the opposite. Getting an upgrade out of Starwood as Gold is like pulling teeth. As Hilton Gold, upon checking in for all my stays this year - it starts with 'You've been upgraded to Executive Floor as a Gold member.'.

At HKG where they couldn't upgrade me to Executive floor because some floors were closed, they automatically told me I'll still be getting the benefits of Executive floor. (Free buffet breakfast daily + free local calls - sounds a lot like Starwood Platinum, does it?)

ec336 - I've noticed this selling upgrades thing too. I was told that Gold only gets upgrade to a better room within the same category that we booked. So whatever they sell us is usually more than one category. The Sheraton in my case was absolutely overdoing it. A total of 5+ times asking me whether I wanted to pay the $30. When I tried to ask for a room with a view as booked, they once again tried the same extortion technique before trying to understand why I am asking for a better view.

Hilton or Starwood? Hilton for me definitely especially since most of my hotel stays are in internationl cities.