editing the save should not be done, as it can break the game, both Anna and Sam share with Adrian are done after you are already with them. Anna is after checking Adrian's pc, while Sam is by inviting Adrian to the pool after you're sharing her with Ken already. You can check the discord guide.
When having the conversation, really early during gameplay, after he has the discussion with Josef, you can give him $20k. Have in mind he ONLY LEAVES for the endings, he'll continue to be at his room and at the places he normally is at.