Quote Originally Posted by AngryGumball
I think you underestimate the level of each shinobi and how they were building up the enemies at the time setting of that time. Kabuto was being made out to be an equal and a rival of Kakashi.
I completely disagree with your post about Kabuto being an equal with Kakashi.

I think Itachi was suffering from a few things one of which was his eyes were going blind, not to mention the ailment you mentioned where he kept constantly throwing up blood.