No thanks.

Sometimes it's good to have a binary choice, though I suppose there really isn't such a thing as a true binary choice in a game like this. But as others have said, you're either for the Imperials or you're for the Rebels. Or you don't care, so you help neither.
Leading my own revolt? No thanks. It works in New Vegas, but not so much in Skyrim. Firstly, what would you do as High King/Overlord/Whatever? I'm not a huge fan of becoming leader of a province because, frankly, leading an actual
province would realistically require a lot of bureaucratic, paper-pushing guff that I don't need in my game. I mean, really, as High King, you're not going to be running around killing bandits or combing through ancient ruins. There are adventurers for that! You owe it to your people to stay alive and lead your subjects well (or keep them in fear during your iron reign of terror, as the case may be); you can't be off on your own killing dragons. Secondly, how do you even BECOME High King? In theory, you could just kill everyone in your way, but then you could realistically only be an evil powermonger-- what if I want to be a benevolent ruler and help the people of Skyrim? The reason the Wild Card questline works in New Vegas is because you have an army of robots that only need to be reprogrammed to enforce your will. In Skyrim, no matter how android-like they may seem to you, the residents are not robots-- you would need to win their hearts and minds (unless you're an evil tyrant, of course). Thirdly, "All hail High King of Skyrim, leader of the Nords, his majesty...Dru'Shakkar...?" Ok, I'm not necessarily against it, but really, how could a Khajiit become High King of Skyrim? Or an Orc? Or a Breton? Or anything BUT a Nord?
None of what I just said is concrete fact, just my opinion. I just don't think the whole Wild Card idea would work in Skyrim.