Take a look at what Tobi says

'Some weirdo takes you in and starts telling saying all these shocking things.'

Pretty much refers to Obito and Madara's first meeting.

But I guess Kishi pretty much planned it from the end of the first Naruto series, no point in throwing the 'Kakashi Chronicles' In there if it wasn't going to have any meaning later.

It's just a topic that's been brought up about Kishi making a last second move, some people are retarded tbh.