Nice job as always, Chie!
I don't ever think this particular aspect of Itachi's character was ever addressed before and explained as well as you did. You've definitely shown that Itachi still had a more humorous side despite everything he went through.
Personally though, I feel that when he meets Sasuke again to fight him, his comments probably weren't intended to be all that funny, considering the magnitude of what he was about to do. But nonetheless, they definitely do allude to his kindheartedness and true self which we thought was just an act at that point in the story.
Again, wonderful thread, I think it's my favorite one of yours
