Board Thread:Theories and Speculation/@comment-36512555-20200202084241/@comment-9782468-20200204230050

The deal with Obito was that Obito spared Konoha/Sasuke. That's it. He could have killed him after but never did. And Itachi could've just used Orochimaru to get into Akatsuki. Honestly getting into Akatsuki shouldn't be too hard for Itachi.

Idk what you're talking about with the tailing bit, but that should be within Itachi's skills as an exceptional anbu so I'm not surprised.