Pain would win till 3 but they would ultimately get tossed around in Scenario 4.
1. SM Naruto already happened in the Manga despite Pain already battling the village before his arrival. Naruto would have been beaten had not been for the intervention of the Kyuubi and Deva was unable to use his ability for a set period of time when this fight initially started so Naruto basically battled 5 paths with the most powerful being inactive at the peak of the battle. When he got his powers back, SM Naruto only had Deva and one more Path to battle but still nearly lost. Still believe that Naruto would lose.
2. Ms Sasuke, Pain should have the upper-hand here. Especially with no intel on Pain, that's a bad match for him.
- Sasuke's Genjutsu is useless, not only does Pain have a strong Genjutsu/Mind barrier from what I recall as stated by Inoichi, Nagato is able to pass chakra through the rods to break the Genjutsu anytime as this happens constantly.
- Amaterasu is useless as long as Deva and Preta are around but remember, adding Amaterasu to this won't help him at all. Even after being healed completely(Middle panel:
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), he immediately dropped his Susano'o(V2) level after using Amaterasu just once as even Obito was stating in the bottom here
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and at this point, he had only used V2 against Danzo during the first exchange of the fight. V4 seemed to be heavy for Sasuke while incorporating another powerful technique like Amaterasu. I don't think it is a wise move for someone that constantly has to hold Susano'o to defend against attacks from Pain. If he drops his Susano'o he's extremely vulnerable.
- Summonings would not be taken down by Genjutsu, Amateratsu the only choice but how many burst and how many summons would be there for this to take down? Multiple with Susano'o? The second point above explains why this is a hard option for him.
- Arrow is very fast for but again it can be absorbed by the barrier of Preta since the point at which it would be fired would be seen by them, the point in which the arrow is drawn. Asides that, I can see the possibility of it being deflected by their chakra rods
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if timed properly. The path have a set formation so the arrow would be aimed towards the direction where they're at, not far fetched to have one jump in front awaiting it and absorbing it in front of the others
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Matter of fact, he's usually in front.
- Kirin? Would this come out before CT? Might be the decider but not sure Pain would be sitting around for this to happen.
One of the main reasons why Sasuke would lose this fight is because Pain is familiar with the Sharingan techniques as seen in his fight with Naruto and Itachi when he came back to life
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, however Sasuke would have to figure out how his own techniques work and that's nowhere near easy for him. Ultimately I would give this fight to Pain regardless.
3. Pain wins this fight. Orochimaru and Tsuande won't change much and there's nothing they can realistically do again CT.
4. Pain would lose here without a doubt, Ay+Onoki combo is something they cannot stand against. Absolutely no chance at all when you then factor in the speed and then the Hidden Mist Jutsu to accompany this. Naruto used smoke bombs and dust cloud to hinder them. Even this was used against Madara in order for the duo to destroy his Susano'o. Pain would be destroyed, then there's Gaara to add to the fray. Pain loses this one