So I have a concern I would like addressed, if he goes confrontational still chooses to stay the weekend knowing there's a guy who he know is a psychopath out for revenge in his house and he stays because of grades is unrealistic as hell, you would do remediation classes, take some extra work or do anything else, but you would not choose to delay the trip back home.
I understand that if the player goes back home in the first weekend and confront Darien you lose the main antagonist of the story.
But the cool aspect so far is that you can instantly add another antagonist and this one is entirely the player's fault, you can frame that he doesn't feel confident going alone, so he ask Jason or Gary for help, later on after the drama is resolved entire family is thankful, Jason/Gary gets everyone else's contacts including of your gal and mc is oblivious that in order to kick the fox out of the hen, he invited a wolf, and because he is thankful to the wolf he is late to realize it.
Even with all the signs showing it is happening including every weekend he goes to visit the family the wolf goes too and everyone is getting extra chummy with the wolf as well, this could even help with the sissified content, since Jason or Gary can also directly influence the player and he would be oblivious due to the fact he still see them as the truest pal of all time.
Besides that point I like where you are going with your game. If we could choose who takes the family I would vote Jason, between him and Darien he seems the less insane, and I can actually see a healthy angle where he influences and corrupt the protagonist first and later the family. Still this is your game and your narrative, so I will not meddle in it. I just hope the narratives gets more tight later on