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If they weren't allies, how could Obito just think about capturing both the eight and nine-tails, and win a war in which he was challenging the 5 great nations?

His only weapons were the clones of the white Zetsu, which, regardless of their "copy ability", were such a big failure, and the Gedo statue, which was his trump card. In that way, Obito would stand against an Allied Shinobi Nation, who weren't weakened by the Edo Tensei reanimations, but obviously, he wasn't expecting that Kabuto would search for him and offer a helping hand, so I think that Obito was overestimated by Madara to think that he could manage a plan with such a great magnitude.

And as second thought, what were his plans for resurrecting Madara? Losing Nagato's 7th path, I'm curious how he would've managed this part of their plan. It's kind of luck for both Obito and Madara, that the events turned out as they are right now in the anime...

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I guess Obito will lose the war.

Obito seems to have underestimated the 5 nations. Maybe because he thought that he can take advantage of their previous wars and conflicts and never expected that the alliance will truly go in war as one allied shinobi rather than fighting for their own nation.

As for plans on resurrecting Madara, I don't think he still plans to do so since he said that he wants Nagato to use the 7th path on him and his current actions shows that he wants to be the Juubi's jinchuriki himself and the one to cast infinite tsukoyomi and I think he underestimated Madara on that one too.

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I think your hint goes in the right direction, Madara had counted on Nagato to resurrect him, he didn't expect Nagato to betray their plan. And then Madara, with Obito and Nagato's help, could have taken care of the five nations.

From wiki:

Tobi was surprised by news of Nagato's death and, more so, his "betrayal", having wanted Nagato to save the Samsara of Heavenly Life Technique for him.

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  • but as far as I know, the user of the Rinne Tensei would die after using the jutsu
    – Rinneg4n
    Jan 20, 2014 at 11:11
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With the rinnegan, he can defeat the five kage. Also he had gedo statue and 7 tailed beasts at his disposal. If you consider that kabuto never met him, then there would be no itachi and no previous hokage and sasuke would have been on his side. With an EMS sasuke, he can easily win the war. Even if sasuke never joined the battle, he was able to take on kcm2 naruto, bee, kakashi and guy. He would have found a way to retrieve some part of 8 tails and 9 tails chakra either by using white zetsu or by his chakra absorption and gone for an imperfect transformation again by making kakashi force him break the seal by a chidori.

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  • Can you provide any sourcing or citations for this?
    – kuwaly
    Nov 25, 2018 at 5:52

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