if the man Itachi spoke to was Madara, then Madara was alive until really very recently... i don't know, not criticizing here or anything, as what you say is also what i believe. just saying that the timeline is all messed up.
Yeah well, I say that for a variety of reasons since;
- This is a visual manga, and as such, visual clues are to be picked up on. Tobi suddenly having long hair is
certainly a clue left to us by Kishimoto. Why would Tobi randomly grow his hair and then cut it again? I don't buy into the fact that there was only one Tobi.
- Obito received a 1 in the databooks with regards to intelligence. Am I to believe he trolled the shinobi world single handedly? lol.
- Minato and Itachi, cited as being among the smartest characters in this manga, were not wrong. Minato had an initial hunch that Tobi could be Madara, whilst Itachi was especially sure that the man he met was Madara, and for good reason to.
- Kishimoto confirmed in an interview that Madara and Tobi do know eachother. If Tobi really is Obito in body, mind & soul (which I doubt at this point in the manga), Madara would've lived up until
at least Kakashi Gaiden.
I just wholly think Madara was the brains behind the operation whilst "Obito" was the 'brawn' (if you can call it that). After all, Madara would've been over 100 years old by that point and surely in no condition to fight.