Anton Crane Bug * Spoilers *

[ComradCasper]

So I'm doing his main quest to retrieve his data from the outlaws. I betrayed Cassandra after agreeing to help her but shot her in the back. Also got Porter to leave peacefully. 

I'm trying to either turn in the data to Anton or keep it, however as I'm roleplaying as a total d-bag, I want to convince Anton to kill himself. However I don't get the persuade options that other players seem to get, despite my persuade skill being 50+. And I keep reloading to different points trying to remedy this, and I either gain certain dialogue options but lose others? Like I can't seem to tell him about the " Black marks and paperwork " in response to Jameson's death in one save, but in another I can. Like wth is happening? My stats are high enough and I've been a jerk to him the entire time, what's going on?