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I find it really odd and confusing that the six paths were all people Jiraiya had encountered randomly in his journeys. Jiraiya recognized them all during that last fight and they were all there in his chronicles.
One or two guys being the same can be thought of as a coincidence, but all six of them?
I don't think a canonical reason has ever been explicitly spelled out, but the following seems the most logical to me:
Jiraiya is an old, well-traveled, highly skilled ninja. It makes sense that he would have encountered a large number of people and built up a sizable number of memories about many of them.
Having been taught and rescued by Jiraiya, Nagato (aka Pain) would have had ample chances to build up a certain familiarity or even obsession with him: Jiraiya likely related a lot of stories to him, including the various people he had met. So Pain is likely to have at least a second-hand association with these people, and may have had an inherent interest in those meaningfully associated to Jiraiya.
Nagato had to witness the deaths of his friends and comrades even after Jiraiya left. Feeling that they could have been prevented if Jiraiya had stayed with them, he blames Jiraiya and wishes to inflict the same misery upon him. In other words, he wishes to shove the ignominious deaths of Jiraiya's comrades in his face.
Nagato has a keen awareness that Jiraiya is one of the most powerful ninjas around, and expects him to be one of the biggest problems to deal with. As such, anything that will put him mentally off-balance will be a major benefit. He knows that Jiraiya is emotional and cares about his comrades, so what better way than to make him fight them (or their bodies, at least)? As I recall, this worked for a brief period of time. At the end of the fight, Nagato says that if Jiraiya had just figured out the secret of the Six Paths of Pain earlier he would have won. So it's possible that even a matter of a few seconds spent in surprise or uncertainty about fighting (the bodies of) his comrades made exactly that difference: if he had remained calm and collected the entire time he may have figured things out sooner.
