I was discussing this with K-oz on another thread and just seem like making a thread would be better..
There is a hole in Itachi's timeline when entering Akatsuki created by Naruto's author.
Everyone thought that Itachi entered Akatsuki by killing his clan but if you remember correctly he was part of it when Oro was still part of Akatsuki.
Oro left 7 years before the timeskip.. Itachi was 18 then. This means itachi was 11 when he fought oro and cut his hand off... which also means Itachi was not even part of Anbu yet AND he didnt kill his clan cause it was a requirement to enter Akatsuki.
So.. maybe this means something for the future story or the author made a BIG boo-boo..