Barbara died because of a Deadly Prank by Walter
It is possible that while Barbara was babysitting Walter, he set up a prank to scare her on Halloween. It involved scaring her when she reached the hallway up stairs, but when he scared her, she tripped on one of the roller skates and fell over the banister, and broke her neck. She was quietly buried and her mother gave some help in providing small details to the comic publishers in order to make Barbara's last moments as a hero, trying to protect her brother before being consumed by supernatural forces. And Walter was so traumatized by his guilt, his mind blocked it out and he believed she was killed by some other force involving the so-called curse his mother instilled in him. Barbara accidently killed her boyfriend Rick and was Driven to Suicide
Its possible that after his first attempt to scare Barbara, Rick tried to get Barbara's signature scream out of her by pretending to be the hooked serial killer but this led to him falling off the bannister while Barbara was "fighting" him off, killing him. Upon finding out she accidently killed her boyfriend she Goes Mad from the Revelation, cuts her own ear off, and disposes of his body before killing herself. The severed ear points to this interpretation along with the comic suddenly becoming vague about what happened to Barbara once she goes down to where the hooked man fell. The severed ear could be referencing Van Gogh and how he cut off his ear before he went mad and committed suicide while the comic could be hinting that the whole "surprise party" part of it represents Barbara finding out she killed her boyfriend and going crazy. Milton was Driven to Suicide
The flip book might have been a visual metaphor for his desire to escape his circumstances for whatever reason. The family might not have found the body. Edith’s son is named Gus
Edith mentions that if she were a boy, Dawn would’ve named him Gus. She could’ve remembered this and named him in honor of her family.- Jossed, he's named Christopher per Word of God.
Milton died in the tunnels and was transported to the world of The Unfinished Swan; the wine bottles are also involved
Giant Sparrow revealed Milton is the King from The Unfinished Swan, and some of his paintings can be found in tunnels of the house. In the tunnels, there are also a couple of empty wine bottles. Perhaps Milton used the wine in his paint, caught some of the fumes, and had a little bit in the tunnels. He fell asleep, suffocated, and popped out of existence. The music in Barbara's story is not a simple Shout-Out.
The game actually takes place within one of the many timelines of the Halloween franchise, and Barbara's killer, unbeknownst to anyone In-Universe, was Michael Myers himself. Why was he there? Maybe he took a vacation from Haddonfield or something, IDK. And why would he be about and killing in 1960 when he's just a kid and hasn't even committed his first murder yet? He borrowed the Necronomicon from Jason after the events of Freddy vs. Jason vs. Ash to go back in time to The '60s and kill people... for some reason. Rick was also killed by the person who killed Barbara that night.
The more common belief is that Rick was the one who killed and made Barbara vanish that night, but it's also possible that Barbara's killer also killed him. The comic story indicated he was on crutches the night of her disappearance/death. Even though the portrayed letterman jacket indicated he was some form of athlete, and he was a decent bit taller than her, a fit young woman like Barbara has at least a greater chance against someone with a broken leg who relies on support to stand. If not in a fight, at least to run away from him. If anything, the person who killed her also took advantage of his physical disadvantage and killed him. Either taking him along with them in their own vehicle or stealing his if he had used one to get to the Finch home. Which is why he also vanished into the night the same time as Barbra. The curse clearly has no compunction against going after spouses with its misfortunes. Who's to say it wouldn't extend to boyfriends either? He may have been touched by the curse before, given his broken leg in Barbara's story. Who's to say that final night wasn't his biggest run-in with the Finch family curse. Edith discovered her pregnancy late
It's hard to catch but her "Until I found out about you" line could mean that she never knew she was pregnant until she was about 22 weeks along. If we remember that she passed away of maternity complications, perhaps, Edith never knew she could make it through childbirth because she never found out about any complications before that point. The Finches are descendants of Morpheus
It could be why their family is rather imaginative and could possibly explain why stories are so important to them. Edie was immune to the curse for most of her life
The curse doesn't just want the Finches in question to die, it wants them to die in a cruelly, desperately ironic way. As long as Edie accepted the curse as a story, she would Face Death with Dignity, which wouldn't be enough for the curse. For her, the curse had to play the long game and wait until her dream of living in a house with her family went sour when Dawn abandoned her, as only then would the situation be sufficiently ironic.
