Originally Posted by DJ_Iceman

You raise good points. Personally, I almost never care about an upgrade so don't go out of my way to seek one. But when I'm with my family, and really want a great view or extra space, I generally use calguy77's technique--I pay for it in advance!

But when I want to finagle a better room than I'm willing to pay for, my approach is to call the hotel and ask to speak with the rooms controller. Ultimately, that is the person who assigns rooms and has the direct power to make or break my stay. Yet they're not high enough on the food chain to be screening calls or not usually in the office during normal hours. I make my case, sprinkling in some humor and trying to find ways to establish a personal connection. And I'll not-so-humbly report that my success rate is phenomenal. But again, I only do this on the very rare cases when I care about an upgrade and can't/won't pay for it.