huhh, just smacking naruto would let the kyuubi come out???
I think it takes allot more then a smack to let the kyuubi come out, and even if it did a second time, the moment naruto starts leaking kyuubi chackra, Kisame's sword would just absorbe it.
And naruto dodging a attack from Kisame or Itachi just wasnt gonna happen, like i said, "taking icecream from a 5 year old"
Do you really think Itachi would use something as dangerous as Sasuno'o right from the start or when he had other options left?
I'm sorry but that's just silly, he was one of the best shinobi out there, and good shinobi's dont use there ultimate justsu when they have other options left.
On the Genjutsu, after some thought, well maybe he would be able to cancel it, but no way he could counter it.
The counter genjutsu, relies on the sharingan to see and copy the way chackra is formed and used, but since Itachi doesnt have 2 frogs sitting on his shoulder, performing the jutsu would simply be impossible.
And lol, Itachi did rape Orochimaru

But he was already using Sasuno'o and already being serious.
So like i said, Itachi using Sasuno'o would have been his last option, and i just dont think he would have gotten around to it with someone like Jiraiya as his opponent.
True Itachi was a better genious, but 53 years of being a genious against 21, is to big of a difference to be left out in this equation.