Yes, I think the same: Obito has no direct intent to help Madara with anything.
As I posted in another thread since yesterday I took into consideration that Obito wants to use the Rinnegan for Rin.
And since this morning I even started thinking that Rin could be the one who knows everything, which Oro and Sasuke are now looking for.
We have no hint on her current whereabouts, right? And there are not many persons left who could know something.
As you said, I am pretty sure also: Oro knew about Madara - Tobi, because Kabutomaru recognized Tobi as a fake Madara in an instant (or even knew before).
And for Madara-Nagato connection I think:
Nagato really was just the only person left who was born with the Rinnegan.
(In the poetic/prosa way that would also be in a smoother correlation with the impression Jiraiya first had of Nagato: the special child and blabla…)
Maybe Oro or Madara or both just found it out and where observing him, just waiting for the right opportunity.
This is highly supported by the geographical circumstances you pointed out.
However we still do not know: What was the Uchiha massacre really about? For Itachi its clear, but Madara or Tobi, one must have helped Itachi. For what reason?
Now I have some questions about details which I think are important for further discussing, and I do not like to open a thread for this so I ask it here:
1. Who is older Nagato or Obito?
2. At the moment : who is possessing which and whose eyes? And these eyes for what can they be used and for what not? I am totally confused.
Does somebody has a good overview of this? Maybe an excel tablet… hahaha
Yes I like the part about Rin, though I doubt it's the one Sasuke is looking for, to be honest I think that would make an entirely different debate, but I still think we need another hint from Kishi on this.
It would be awsome if Obito somehow turned to Narutos side, and Sasuke went with Madara. That would one unpredictable fight, but again unlikely. But Sasuke joining the fight is almost certain - I hope
About Oro I can't predict what he will do next, but he might stay out of the war, as he said.
Regarding your question, Nagato is much older than Obito, or well he is same age as Minato. Since his parents were killed in the 2nd war, and he was starting akatsuki before the 3rd war (with Yahiko). And we know Obito fell to Madaras cave in the 3rd war. Also Minato was trained by Jiraya at about the same age as when he left Nagato, yahiko, konan.
About the eyes, yes that would indeed be good to summarize it up, lol, specially since so much debate about has been going. Some even say Itachi has Madaras eyes, which seems unlogical to me though.. Nonetheless I think there is only 1 set of Rinnengans, but they don't seem to have Madaras sharingan powers, cause if they had why wouldn't Obito use susanoo etc? The rinnengans from the other paths of pain - I believe they just appear through the chakra stakes.
And there are just too many sharingans to count xd
Besides I made a small discussion on the connection between Madara and Yahiko, since Obito could never have known Yahiko. It's here:
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I have some strange feeling that oro was involved with Madara and the beginning of akatsuki, but who knows
