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Would the Mugen Tsukuyomi plan succeed ?
Now when I think about, there's really a lot of complications.. like would he made the same decisions or not ? And the most important - would he also give kakashi his eye? If yes I think Sasuke would have no chance of achiving what Obito did. Obito basically went so far only because of haxed kamui which let him do whatever he wanted but what's more important kamui required only 1 MS, but you can't awaken Susano'o with only 1 MS so it would be game over for him really soon. He would probably survive fight with Minato but I don't see him surviving kage's sumit without Susano'o.
So let's just guess he wouldn't give his eye to Kakashi and would awaken MS in both eyes.
I think the easiest way would be to just switch Sasuke's and Obito's places, so Sasuke would be in team Minato and Obito in team 7 and Itachi would be Obito's brother I guess.
Now they're 2 scenarios :
Both starts same, when Sasuke saw Rin's death and awaken MS in both eyes and decided to help Madara.
1) Sasuke made different decisions - how would he lead akatsuki ? Would he also decide to help Itachi with the clan massacre or would he try to stop him ?(this probably could end even here lol)
Would he take interest in Obito after he defeated Itachi and would try to manipulate him ? Would he team up with Kabuto ?
2) Sasuke followed exactly Obito's path - Okay... so we're starting with Minato's fight. He would propably give him harder time than Obito did due to the Susano'o, but still no chance of winning - different league.
Now this would be probably the hardest thing he would need to do - saving Obito during Kage's summit. While Obito could just chill and make kages listen to him thanks to his Kamui because they couldn't do anything to him so there was no choice but to see what he has to say - Sasuke would probably have to fight all 4 kages and we can only speculate how skilled Sasuke would be after training with Madara, but I still don't see how would he survive. I guess only Perfect Susanoo would be enough "fear factor" to make kages listen to him without fighting, but can you awaken it with just MS?
Anyways let's move on and guess he somehow survived and declared the war.
Next fights would be ez - even "original" Sasuke back in those days would win, so older, trained by Madara would negs fodder Danzo's guards and would have no problems defeating Konan.
And now the fun part begins - taking the Rinnegan from Nagato
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With Rinnegan, PS and his Six Paths of Pain he would easily beat Naruto and Bee in the forest, but let's go further - the fight was so long that Naruto and Kurama finally became friends, so Sasuke would now have to deal with 2 tailed beasts. Now this could be rough and they would probably fight till Madara arrives, but as soon as this happened
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Not even talking about Sasuke becoming jinchuriki
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Conclusion ? He would have rougher start, but in the end, I think Madara was probably right and with Sasuke on his side he could won.