It is impossible to know what he was thinking before rebelling against God. We are led to believe he is very intelligent, and there's also reason to believe he knew God very well. But there is no figuring out what he was thinking that would answer your question.

If everything he does is to pissed off God, then does he even know the consequence of pissing off God before the first time he attempted to piss off God?

What makes sense is that he is actually so self-deceived that he thinks he can actually win this. For instance, while Jesus was on the earth, he must have thought (so it seems) that if he could kill Jesus, that "eternal life" (since God IS life) would die. He could force a contradiction, force a point of no return. Jesus, as a human, had emptied himself (Phil. 2.7) and so had laid aside some of the prerogatives of deity. At that point, then, it's possible that Satan perceived a chink in the armor, so to speak, since God was actually human, and if he could just kill him, it would be a game-changer. Obviously that didn't work.

After that point, though, he seems bent on pulling as many away from God as possible to establish his own kingdom. If you've seen "The Dark Knight" (and Heath Ledger's brilliant performance), we learn that evil doesn't need a reason or even a rational pursuit or purpose, but only evil for evil's sake.

Does satan even know or realize how powerful his enemy really is? What drives him to think that he has the slightest chance to overthrow an omnipotent, omniscience, and omnipresent being that created the whole universe including himself?