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Pain stumps. Even if you give him knowledge and stuff it doesnt stop him from having the ap advantage and hax advantage and numbers advantage and AOE and jutsu versatility advantage and Pain techincally also already has knowledge on Oro themselves
 
Orochimaru takes this, in my opinion. While Pain may have an advantage in AP it's not like it means much since it goes to waste against Orochimaru's body type. That guy is basically un-killable in Naruto because of his snake like body that absorbs physical brute force like (quoting SpongeBob - "like some sort of spongey material"). So things like the Almighty Push while it will knock him around and most likely break some things, like a second later he's back up on his feet and ready to exploit that 5 second weakness. The closest thing Pain can try to "kill" Orochimaru is explosive (and hopes they incinerate his entire body, or Soul Stealing, of which means he's got to get in Orochimaru's personal space to achieve which will make easy way for Sasuke's sharingan genjutsu.) The planetary devastation can be used to "seal" him in a sense but just like Naruto he could dig his way out.

As for the versitality, I'm sorry but... HA!!! Orochimaru has basically almost everything Pain has and more. He can match chakra absorption with chakra absorption, giant summoning with giant summoning (and like manda's his snakes are versatile enough to fight two giant monsters (the toad and slug), he can reanimate the dead, activate genjutsu (something Pain has no counter for), he can attack with an endless amount of snakes, he can activate the Giant White Snake mode to both possess and eliminate a Pain body or allow it to become damaged so it's vaporized blood will paralyze, the list goes on.

And on top of that Orochimaru is a genius both jutsu wise and tactical wise, with prep time and knowledge you just allow him to exploit every single weakness Pain has, and there's a few biggies. So Orochimaru can simply attack from a close range, mid range, and long range at the same time, and toy with Pain who for the first time in his life will be the one overwhelmed by numbers and an enemy he doesn't fully understand.

Orochimaru, high difficulty but I'd say a good 7-8 times out of 10.
 
If this was a fight with no preperation I would have given this to Nagato, considering even if he did possess Sasuke's sharingan during the period he did Sasuke did not have Mangekyo so the tsukuyomi was not available so breaking through a normal sharingan genjutsu is not impossible, Genjutsu is not an actual weakness for them it is just the most effective weapon against them considering fighting them hand to hand is impossible due to the rinnegans shared eyesight and the the Petra path's ability to absorb Ninjutsu, it took a very high level genjutsu to trap them and not an ordinary one, but since this is with prep and full knowledge I would delay my vote a bit. Orochimaru with full knowledge and given prep is a bit much considering the guys intelligence.

I don't believe Manda would be able to take Pain's summoning especially if that multi-headed dog is there and it has been shown Pain is able to summon multiple summonings almost all of them even at the same time. So that would be difficult, and while he can summon multiple snakes the almighty push could as easily deal with all of them including Manda, considering Pain was able to simultanously incapacitate all 3 Toads with one push. But my main problems lies with the 6 of them against one of him, he was unable to beat a 4 tailed Naruto but he did not lose also but now he is going against six of them with almost the same stat in speed and strenth if they were able to fight Jiraiya and Sage mode Naruto in hand to hand combat, while Pain is not aware of Oro's full capablities he does know a good deal of hi fighting capability still since Orochimaru worked for him. Also the body steal with the great white serpent would not work on any of the path considering for one they are merely dead puppets and since he just stole Sasuke's body he would not be able to use it for another 3 years. As for the Dragon God, that's tricky but not really unbeateble with the Pain summonings alonside the Deva path. As for how to kill Orochimaru though, a combination of the soul steal and chakra absorption and chakra rods would work. As for Chibaku Tensei, it took the combine strength of Itachi, Naruto and Bee to destroy Chibaku Tensei and while Orochimaru could easily use Dragon God I don't think it possesses enough physical strength to escape it, unless he does the same with Naruto where he dispels the transformation and leaves a huge gap to escape from. Well this is Orochimaru without prep.

Is Orochimaru allowed to summon Edo Tensei's considering if he is he could just as easily summon all 4 Hokage's, wait they were sealed by the 3rd, but since this is with prep he might consider going to the village and get them back along with his arms

No vote for now, I have not yet thought of how Orochimaru would fight against them with prep time.
 
It does not matter if it's perfect or not considering during the chunin exams he was able to summon the 1st and 2nd just without personality, If he has Edo and he has prior knowledge and prep time, he should take this.

Since it's obvious that the first one he should take down is the one to ressurect the other Pains, with both the 4th and 2nd hokage that should be easy with Hiraishin, while the Deva is distracted by the 1st Hokage while he and the 3rd deal with the others. As for the next ones should be easy, dealing with the machine one is easy and summoner one coud be dealt with by summoning Manda and using the Serpent God form to deal with the summons alongside the 1st, 2nd and 3rd deal with the other paths while the 4th deal with summoner. Then the Deva and the Petra path are left, same tactic lure the Deva Path away while someone deals with the Petra, the Deva would be a longer battle but since Edo do not really rely on Orochimaru for Chakra this would be easy, finally Nagato himself would probably be found by some means and since Nagato is already weaker dealing with him should be easier.

And this is not even considering summoning some of the other possible Edo he could have made like the Kazekage.
 
Basically with Edo, Orochimaru would be able to win pretty easily, without them would require using jutsu we don't even know if he can use or learn in time and we might have to make up new ones or would be wether or not Orochimaru could unlock the Mangekyo and it's abilities, the Tsukuyomi in particular. The Amaterasu would probably work on all paths except the Petra and Deva path.
 
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