When you read back, there are a whole slew of shots of Itachi looking tormented. That scene in the rain when it was assumed Sasuke died fighting Deidara, a lot of his reaction shots during Akatsuki meetings--even when we first meet him, they were there. I'm thinking of his finger twitching on his cup when he hears Sasuke approaching the teashop. The way his blank face is drawn in the manga when we first meet him looks less blank and more melancholy, IMO. The fact that his first impulse is always to talk, not to throw a punch.

Just little things.

I would argue that since Sasuke's conversation with Madara, chapter 416, is actually PRE-Hachibi fight (or at least it must be, based on the time frame), and then during the Hachibi fight, we actually get a mini-Team 7 flashback before Sasuke fights to save his team, who just fought to save him--I would argue that it's mot necessarily bad storytelling so much as misleading storytelling.