#1. "Check Your Privilege" Ends Conversations Instead of Starting Them
By now, you're really getting pissed off. You're positive you know who your enemies are, and you're positive their background prevents them from agreeing with you. You feel I'm distorting the whole point of "check your privilege." To you, the phrase is noble. The phrase is simply beseeching the wrong-minded power elite to engage in self-reflection and see how their socialization has led them to be narrow-minded, oppressive, and wrong.
I've had friends explain that to me -- "check your privilege" is only trying to start a dialogue. That's almost the equivalent of saying that "check my cock for your wife's lipstick" would start a dialogue about the state of one's marriage. The phrase is insulting. It's a shortcut allowing you to dismiss the opposing views of your adversary. It does absolutely nothing to illuminate.
"Look, I explained why you've been socialized to understand nothing and always be wrong. What's the problem?"
If you're a black transsexual woman arguing with some white cisgendered male and you truly want to explain how his "privilege" prevents him from understanding your point, your struggle, or simply you, then spouting "check your privilege" isn't going to help. "Check your privilege" fosters no mutual understanding. Why not talk about you? Explain you? Share you?
What do you want: to be an understood, accepted part of the world with an equal chance for happiness and success, or just to tell the people you perceive as privileged that they're wrong? What is your goal? What is your endgame?
"No, not checkmate, White King. More like you're so white and male you don't even get the game."
If you intend only to dismiss opponents, then great. However, if those behind "check your privilege" really want to foster a better world of mutual respect and understanding, I'd encourage them to share information with those they view as their oppressors. Share and explain your identity instead of merely tearing down others. And if you do that, and the reaction you get is hostile, shortsighted, and cruel, well then, at least you tried, and you can hate them with a clear conscience knowing you did your part to make the world a better place beyond speaking three simple, useless words.
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