I like your ideas and the way you think.
Pretty impressive that some Naruto fans can be logical beings.
I also thought a long time that Itachi did many things in a very "un-fiend'ish" way, if you know what I mean.
For example that he didnt fought Jiraiya head on, that he didnt attacked Naruto/Jiraiya by suprise, or that he retreated in Konoha and in the Jiraiya Situation.
Ok, he used the Sharingan and was worn out, but its not the same, he could have killed Jiraiya right theres, and Kisame was also there for back up.
We will soon see Itachi again, and I have this feeling that this time he has something to say to Uzumaki Naruto.
The last sentence in the last chapter made me feel this way... somehow Itachi was waiting for Naruto right there to show up.