Heiners all kinds of funky but he's depicted to be a very good commander Even with his obsession for Annette, i don't think it'd make sense for him to harm Ryan.
I agree Ryan has death flag vibes but I feel like it'll be something else if it does happen
If Ryan lives to the end of the story, I'd be seriously surprised. I'm shocked Heiner hasn't had him reassigned to active duty again already.