He should lose to 6POP especially with Manga intel.
- Shukaku can only use a TBB. Hence absorbing it becomes easy for Preta since it's just one and not continuous which he can't do.
- Asura with the Aerial attacks via summonings causing distractions.
- Gaara's sand containing chakra gets absorbed and weakened or gets blasted off Pain's body. Not to mention Gaara has 0 knowledge on Bansho Teni'n followed by chakra rods shot at him strong enough to deflect a Susano'o arrow as shown in the Manga.
- Chibaku Tensei is an option...Especially seeing he has no intel on it in this scenario and without knowledge it's debatable whether he can successfully destroy it or not if he has no idea on the mechanics behind it. Once it becomes as durable, he fails.
For those more knowledgeable, if Pain uses Rain Tiger at will won't that greatly disrupt Gaara's sand in the sense that it won't be as effective
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? He can control it no doubt but I'm questioning it's effectiveness in a wet state as it may weaken its hold on opponents?
He loses to Obito as well with probably little to no intel on Kamui.
- Teleporting becomes a viable choice if he can beat Gaara with its speed or with little knowledge on that.
- Kamui's time limit cannot be exploited when one doesn't know about the 5 mins interval or so. Even if he knew and Gaara kept attacking, Obito would just go underneath and appear from somewhere else to reset it. Gaara usually senses people via Sensa Kaibyō which involves his special sand containing chakra. Obito would never be caught up with such given the fact that he has his Sharingan which can see chakra so he'll know not to got to that specialized sand that would track him.
- Obito has Uchiha flame formation that can be effective as well.
