Actually, the explanation for this is quite simple (in my opinion) and it lies not in Callista's ideas about Kane, but in the presentation of the story to the player. If Callista had told Kane everything, there would have been no surprises and the game would have lost some of its appeal. So, secrets are dosed carefully and gradually, and even Olivia doesn't know everything (and what she does know, she doesn't tell).
I think that's reasonable...Kane is already playing the role of "Neo, the chosen one" in many ways, and if all the secrets are revealed on top of that, the game could be over. However, I do agree that Kane could have been a bit more savvy and understood a bit more than he should have. But to blame Callista for this.. no, she did the best she could... And if Kane and Olivia, despite Callista's virtuous upbringing, did veer into the grey areas of morality, it's certainly not her fault.. Yeah, I don't really like the fact that Olivia is the girl with the golden spoon in her mouth and we have to do everything ourselves, but it's not appropriate to complain about it either, because as you know, our Kane can rise pretty high (or fall) if you wants to.