- No he simply didn't want "konoha" ninja being involved in it..its a good political scheme to have an uchiha kill the uchiha.. why risk your own people?
- no he was a mere bump on the road.. the akatsuki would have demolished Itachi if they wanted.. however, Obito used itachi.. so you must remember that also.
- Yea with the help of 2 people who were stronger than him..
- Nope sadly nope. Both of the times he was caught off guard.
- He got used.. he was a child.. not blaming him... his thinking wasn't that open, but restricted to the village.
Well, apparently he was willing to let Konoha ninja be involved once he told Itachi that if he didn't do it, then his own men and the rest of the available Konoha shinobi would annihilate them.
Yes, Itachi was a mere bump in the road that caused Obito to stay away from Konoha for 7 years. For whatever reason, Obito didn't kill Itachi. I doubt it was only due to the deal they made.
Orochimaru is the one that intiated the fight the first time. Oro was attempting to catch Itachi off-guard, but failed. The second time, Oro emerged and claimed that he was going to takeover Sasuke. He was completely aware that Itachi was standing in front of him. He wasn't caught off guard by Itachi, he just didn't expect him to be in possession of Totsuka. Claiming Oro was caught off-guard is like claiming Minato was caught off guard when Madara sliced his arm off and kicked him away. No one expects to be defeated.
Yes, he did have the help of Naruto and Bee. However, prior to Itachi interceding that fight, they were about to have their souls ripped out by Nagato.
The last chance to stop the massacre was KA, which made it evident that talking was getting pretty much nowhere at that point. KA failed. Itachi had a choice and made it. He wasn't exactly used, he just made his own decision and stuck by it.