Potential Spoilers for the events Season 6-8 of Naruto Shippuden
In the Jiraiya vs Pain fight we get the following information.
Konan is a former student of Jiraiya, who is also the Angel of Amegkure and Pain who has the Rinnegan is the leader who defeated Hanzo. During the fight we learn of the six Paths of Pain, each who uses a different unique abilities while sharing their field of vision. Jiraiya was confused how could six people have the Rinnegan when only Nagato had it.
This is the setup for the sequence of the events leading into the next season.
Jiraiya recognises Yahiko, and then the body of pain that he pulls into the toad. He then decides to go back out and realises that ALL the paths of pain are Ninjas he'd seen/met before. And then the realization "The real one is not among them." This confuses me since we know Nagato can make any dead person a path of pain (the new Animal Path), Why would he chose those particular individuals that Jiraiya knows? Infact how did he know Jiraiya knows them?
And thus the question, How/Why did Nagato choose the "Paths" of Pain?
Additional Info: He chooses the following paths of pain
the 5 shinobi that Jiraiya encountered during his journey: The Puppeteer, The Waterfall shinobi, The Fuma clan shinobi, The Grass Shinobi, The Priest. The sixth path i.e. Yahiko seems obvious due to their connection. But again using the other 5 seems very coincidental.