Im going to assume and this is a big assume that madara implanted a memory inside of nagato that when he came to a certain age or a certain emotional state the memory would have triggered. so thats pretty cool if that is actually the case.
I also say obito seems to want to leave to help is friends, so yeah, hes not listening to madara about loss and whatnot so when rin dies on a mission and obito finds out, he no doubt comes to terms with winners and losers and agrees to side with madara.
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