I definitely agree on the situation with Chester's epilogue.
Also I feel the hinted at threesomes in every route felt really awkwardly forced. Maybe I'm just too monogamous for my own good but I don't really enjoy Eric basically setting himself up to be in a cucking situation (specifically in Harold's route and Spencer's route.)
I appreciate that Dozer's route only has that pop up if you have Chester's perfect ending but even then, that kiss CG at the end with the three of them put Eric in a third wheel position and I didn't appreciate it personally.
All in all, I still love the game despite it's occasional flaws (and my personal annoyance over the way that dishwashers are talked about in most routes as if the other person had never heard of one in their life)