I liked that manipulation comment Orochimaru had somewhere around the middle/end of the chapter. It seems like he can easily acknowledge that when Sasuke fled from the Hidden Leaf and sought him out for power, it was a change for the worst in Sasuke. The same could be said about how Tobi affected him, whether Orochimaru actually knows Tobi or he has simply been able to put everything together. He did say he'd been watching from Anko's Cursed Seal all this time. Maybe that's the whole reason he knows everything about what is going on in the world right now.
Considering that Oro's intent was to take Sasuke's body, I don't know how he
wouldn't see that as bad for Sasuke. But I see what you're saying. Oro seemed uncharacteristically human in this chapter.
He might not actually know at all, but when you read it and look at it in the right sort of light, when Orochimaru questioned Sasuke about wanting to meet this person/these people, didn't it seem like he knew them personally? I don't mean he was buddy-buddy with them, just that he knew who Sasuke wants to meet with. Maybe it was just me.
I thought the same thing. Moreover, Oro's subsequent comments made it seem as though he knew what Sasuke wanted know, even subtly discouraging Sasuke from pursuing the truth -- as if the truth is too much for him to handle (ignorance is bliss).
I dunno. I'm trying not to look too much into the dialogue since are quite a few inconsistencies: like when did "the human" become "them", and how Sasuke made it pretty clear last week that he was "going" somewhere to meet Orochimaru, but then he didn't "go" anywhere. I'll give Kishi the benefit of the doubt and assume it's a translation issue, and not that he's intentionally try to screw with his readers.