Itachi already anticipated if Sasuke wouldn't turn away from his vengeant ways that's why he gave Naruto the crow job. I don't think he would be devastated to find Sasuke trying to destroy Konoha.
There really is little point for the two to meet up and fight again. I doubt Itachi would go all out against Sasuke even now. I doubt Sasuke will ever be convinced that their clan was a murderous bunch of drows and that Itachi was the only one to see his way out of the Underdark. It would be awesome however if Itachi would find it in himself to do the deed of killing Sasuke himself if they do meet, but that is highly unlikely. It would be also awesome if they do have a rageface conversation.