Originally posted by: RasenDori
i dont think that the point was to test his actually strength. itachi knows that he is strong.
consider what is the most important thing to the ninjas of the leaf: friendship and peace.
if itachi wanted to join the akatsuki he must be willing to break free from what others consider to be the weakness of the leaf (which is actually there greatest strength)
the greatest extreme of this is killing his family and by doing thisitachi is able to prove that he can break away from his humanity and become a tool, the way of the shinobi.
i feel that he failed in that attempt and feels remorseful, and therefore wants sasuke to kill him for his sins