Re: Itachi's appearance.
Itachi is indeed very strong, and his quotes are my favourites in the series. but it's unbelievable how much he's overrated, he's portrayed as jiraiya's equal and while that places him in the current timeline's top 10, there are various shinobi who are much stronger. he and jiraiya are equal in the databook, and tsunade and oro half a point behind, with kakashi and old hiruzen 1.5 pts behind.
Itachi- subdued Kakashi, Orochimaru, Deidara, died vs Hebi Sasuke because he wanted to.
Jiraiya- forced itachi and Kisame to flee, subdued 4-tails naruto with high diff, subdued konan, defeated 3 pains, died vs pain because he wanted to. he didnt win as easily at itachi, but he also fought way higher level opponents as well tbf.
itachi and jiraiya died within minutes of each other and for the same cause, to help naruto and sasuke. and it's implied heavily that naruto and sasuke surpassed jiraiya and itachi with sm and ms. to me it's pretty clear that kishi intended them as equals. but i don't see people wanking all over jiraiya.
at any rate, there are a lot of characters with much better feats. particularly feats where one takes on multiple top tiers at once, which neither jiraiya nor itachi have ever done.
hanzou- defeated the sannin, wounded nagato
nagato- defeated hanzou, flattened konoha, it took full intel and the kyuubi to stop him, and 2 perfect jinchuuriki and edo itachi to stop him as an edo.
hiruzen- orochimaru and 2 edo hokage
minato- ay and bee, obito and kyuubi
naruto- his clones were fighting kage, enough said
obito- killing 20 jounin, konan with prep, and taking on naruto,bee, guy and kakashi at once.
edo madara- kills 5 kage. ems madara also flattened muu and oonoki without using perfect susanoo apparently.
hashirama- defeated kakuzu, ems madara+kyuubi
kabuto- edo itachi and ems sasuke
sasuke- fights all 5 kage in sequence, although he would have been killed alone he still hadnt fully developed his ms.
i think we can all agree that the above's feats supercede those of itachi and jiraiya. and while itachi has intelligence and shinobi sense in spades, plus great abilities to apply that, also remember that he doesn't have the stamina to implement them fully, except when going completely all out vs sasuke. plus he would have been blind by 22. so in short, a great shinobi with big flaws that are glossed over by his fanboys.