(spoiler) (last theory here than moving to discord to rant) wait, wait, wait, in the benson bad end it says Orlando and Sal went to visit Sal's sister but we later learn she's dead isn't that like super sus and we don't ever hear from them again did they pull a Roswell and go to the masion or something else? but then it made me realise dean knew too why didn't he think it suspicious? and now that I've revisited that conversation is so foreshadowy just like Deans really
That can mean they went to visit her grave or the place she died. we know this is something he doesn't want to talk about with just anyone. He spoke about his sister as if she was alive before he told MC as well. I don't think that's Sus I think that's just part of his grieving process.