Oscar legitimately has no idea what exactly he's doing or why he's doing it other than that a voice in his head, claiming to be the dead "soul" of Beacon's headmaster who has merged with Oscar's soul, has been egging him on to "do the right thing."
The thing is, even when he does leave, Oscar is still in the blank: Ozpin, as usual for his "mysterious, reasonable authority figure" posture, has given him very little context (especially during their brief encounter with Hazel), and has essentially gone out of his way to be as vague as possible.
And its that same vagueness that allowed Cinder and Salem to wrkec everything in the first place: Oz's lack of trust and faith in others, his unwillingness to share the full truth, treating himself like some sort of knowledge martyr or something like that.
And that brings in my hopes and expectations for Qrow this season: thus far, Qrow has proven himself to quite possibly be Ozpin's MOST loyal agent, having shown very little to no disagreement with him.
I wouldn't be surprised if this season gets us moments where Qrow seriously has his faith in Oz tested, both by the secrets he's been likely keeping and the decisions he makes throw Oscar.