I think he was just predicting every possible outcome. I personally liked the fight and how they made it seem like a chess game.
Also i don't think he knew about the genjutsu. I think he was just smart enough to know that pain would divert his focus from it. It's not like he planned that or he knew it was gonna happen. Just look at the pages where he trapped in the genjutsu. To me he look suprised.