@Da Best Ever, I don't think he did a terrible job at spying, considering that Obito was afraid to touch Konoha for the 7 years that Itachi was in Akatsuki. How would he inform Konoha, when the only man he could report to(Hiruzen) was dead? He certainly wouldn't inform Tsunade, she thinks he's a criminal and has no idea of what really went down. Would the elders be willing to tell Tsunade of the intel, considering that they didn't like her? He had no one to even tell intel to. However, he could have somehow informed Jiraiya...but that could be a stretch. I guess that would make sense though, because when he went to Konoha in pt1, after Jiraiya said that he knew there were more members in Akatsuki, Itachi was like "I see now. So you're the one who told Kakashi-san." But he said that when he didn't even know if Kakashi and Jiraiya spoke to each other. :/ I don't think he would be able to take out most of the Akatsuki at once, because they would probably contact Obito and Nagato to help them. He cannot take on all of Akatsuki at once. Also, maybe he expected most of them to die at the hands of the other shinobi nations, so he didn't see any point in even taking the risk. He also wanted to have the fight w/ Sasuke and if Itachi decided to fight either Obito or Nagato, he would overuse his eyes and not be in any shape to fight Sasuke later on. He was taking medicine to prolong his life and using will-power to live. His priorities were first Konoha and then his little bro. He was keeping both in mind. We also don't know how much time the Akatsuki members spent w/ one another. Obviously, Itachi spent the most time w/ Kisame. They spent the most time w/ who they were paired up w/. We also know that the Akatsuki was not always together. We really don't know how much time everyone spent together. The only time they were altogether was when they were sealing away bijuus. There could have been years passing in which Itachi didn't see the other Akatsuki members, minus Kisame. In fact, towards the end of pt1 in the manga it's stated that there was a several years lapse in which the Akatsuki didn't assemble since Orochimaru left them. Obito also stated that he had to hide from Itachi some of his secrets, like Izanagi which saved him from the Amaterasu activation. He probably avoided Itachi's presence anytime he could, so that would make it increasingly more dificult to take him out.
