we don't know much about akatsuki and how powerful they are, but they obviously aren't that elite if they have to be hunting down the (can't remember what they called it) the things inside of naruto and gaara. I think Itachi is seriously overestimated. Kishimoto spent so much time developing jiraiya, tsunade, and oro's characters so we KNOW they are how strong they are, and almost made it clear that together akatsuki is powerful, but any 1 of them is not stronger vs any single one of the legendary 3. (which we also found out when itachi and kisame ran from ONLY jiraiya). I believe oro and akatsuki definitly will have another part of the story connected through sasuke.

I think theres a strong connection like theorized between the 3, sasuke, itachi and oro. Itachi dieing may have something to do with that.