I think I misunderstood your question, do you have a problem with a bug or a choice?
well, with adrian it happens to me that since i paid the 20k fee for him to leave he NEVER left and he is still here and i have done all the shared path with him except the one with anna and adrian. so i don't know why adrian doesn't leave.
but josef if he is able to leave after giving him many drinks after he asks us how we get so much money after paying all the debt (in this new route I still don't do it), that choice will only happen once, as the game tells you “the black bars mark important decisions”, so if you already decided, you will have to start from 0.
ah well, if you are on that route, if I remember correctly is to pay the million of the debt, then give him beer, talk (should come out the dialogue of the decision), if not, give him beer, then whiskey and talk to him until it comes out, you should treat him like garbage.
you can only do this on friday at the entrance.