War arc Obito w/ rinnegan & the jinchurikkis...unless Itachi thinks of a plan he is not winning against Obito at all, because it took Naruto+Minato+Tobirama+Sasuke+the rest of the shinobi alliance to take him down.
MS Obito vs MS Itachi...most people commenting don't realize this but it is a manga fact that Itachi was stronger than Obito and could defeat him at that point. Obito was thrilled upon hearing that Itachi died because then he could finally continue his plans. Obito couldn't lay a finger on the leaf village due to Itachi still being alive and willing to stop him if he attempted to do so. Even Obito admitted this. Also, apparently Itachi does have a counter for kamui, because in the only movie that Kishimoto wrote the entire script for (Kishi wrote it and came up w/ the story line, character designs, etc...might as well be canon), "Road of the Ninja", Itachi saves Sakura from Obito and analyzes kamui. Itachi proceeds to tell Obito that he knows that he can phase out for a limited amount of time and that he knows a way to still hurt him. Obito then calls Itachi "a very troublesome shinobi" and runs away. Kishimoto is basically trying to tell us that base Itachi beats base Obito. Itachi was the only Uchiha who relied on his own power anyway. Sasuke took Itachi's eyes and gained EMS to get stronger. Obito stole the jinchurikkis and took Madara's rinnegan. Madara took Izuna's eyes to gain EMS which evolved into rinnegan, and later stole Hashirama's DNA and injected himself w/ it.
And about some common misconceptions...
1. Itachi let Sasuke break out of his genjutsu. It's stated in the manga that once you are caught in Tsukiyomi, it is impossible to break it. You can only withstand it well and try to bear the pain if you are an Uchiha w/ the sharingan. Hence why kakashi was only able to talk for a few seconds but otherwise K.O.'d
2. MS Obito didn't use kamui to get rid of Itachi's amaterasu activation. The way Obito phases through things, anything touching him follows him (just like his clothes and mask). He couldn't use kamui in that situation, the amaterasu wouldn't fall off or phase through him, it was a part of him at that moment, burning his flesh and he was screaming from the pain. Also, if you look back at the chapter in which this occurs, he uses his 3-tomoe sharingan in order to get it off. Kamui is an MS technique, so the fact that his MS was not activated at that moment completely rules out the possibility of him using it. When you look at Obito once he gets rid of the amaterasu, you can see that his clothes are totally fine and he has no injuries. He used his 3-tomoe sharingan to perform izanagi and change reality and turn the amaterasu attack into an illusion. I don't think that MS Obito would be willing to give up an eye in a real battle against an MS Itachi.
Using logic like" how can Itachi beat Obito when he can pass through anything"...facepalm.
We might as well say that the sage of the six paths, madara, and hashirama stand no chance against an MS Obito due to that.
Obito can pass through attacks, but he has to be intangible right before his opponent hits him for the attack to pass through. If his opponent hits him while he's tangible, he will be hurt and essentially screwed over. That was shown when he lost his zetsu arm to Minato's rasengan, when that shinobi from the Aburame clan caused him to lose his zetsu arm once again by infecting it w/ bugs, and when Obito had to use izanagi in order to change reality in order to save his face and part of his upper body from Itachi's amaterasu activation. That and Konan revealed that Obito could only keep his entire body intangible for five minutes max and he had to use izanagi a second time in order to avoid dying by her paper bombs (he took several sharingans from the Uchiha massacre). MS Obito has quite a few weaknesses that can be exploited if you think about it.