Quote Originally Posted by Super5
Seems a little outrageous to me. From my viewpoint, Itachi was trying his best to kill Kakashi and everyone he encountered in the first fight at Konoha. It's not very clear from the angle that it's drawn at, but I thought Itachi was aiming for critical spots when he was continuously stabbing Kakashi. Besides that, there is the question of whether someone can be killed by Tsukuyomi or not. He also barely missed Kurenai when he struck at her after reversing her genjutsu.
Itachi also used Tsukuyomi on Sasuke....twice....
I think it's pretty safe to say he wasn't trying to kill Sasuke.
I'm pretty sure if Itachi was really determined to kill the Konoha Jounin, he would have.

Also, I could argue that, from your viewpoint, Tobi runs away from everyone he encounters and is an overall coward who talks big. However, we now know that it was all just a deception Kishimoto gave us. Perhaps Itachi is the same way.