On your ask about shipping real people: my rule of thumb is to ask if publishing their diary makes me a historian or an asshole. If they've been dead long enough that their diary would be of historical interest and not be looked at weird in Barnes & Noble, it's fine to ship them or write fanfiction about them or whatever. If they haven't been dead long enough, or they're not dead at all, and publishing their diary without their go-ahead makes me a douche, then it's not fine. Just my thoughts.
This is… actually a really brilliant way to think about it WOW. Thank you SO much for sharing your thoughts with me I’m gonna adopt this line of thinking ahaha.