At first, Kaylee Hackett's death may not seem like much of a gut-punch. After all, not only was Kaylee one of the two Hacketts responsible for freeing Silas, she also purposefully allowed herself to remain uncaged during a full moon, hoping to rouse outside attention (and hopefully help) even knowing full well that she could kill one or several innocent people in the process. But Kaylee wanted to free Silas because to her eyes he was an innocent child being horribly abused, and although she and Caleb should have both known better than to use fire in the forest during the summer as a distraction, neither of them ever intended to kill anyone. What's more, multiple characters - most notably Ryan, Travis, and Constance - have nothing but fond memories and kind words to say about Kaylee, both before and after her body is discovered. Going by the timeline presented in the game, Kaylee - aged around 22 by the time of the game - would most likely have been 15-16 years old when she was infected by her older brother Caleb. She was a teenager with little in the way of worldly experience, trying to help complete stranger when she saw him suffering; as the years went on, it's clear she continued to hold onto her humanity in spite of her infection, and only made the fateful choice to roam free during the game because she was desperate to find outsiders who could help end her family's curse. Even so, her death is entirely unavoidable, being a scripted event that occurs regardless of player choices - no amount of sympathy or strategy will save her, even on a run where everyone else in her family gets out alive. In fact, Kaylee Hackett is the only character guaranteed to die in every single playthrough.No Good Deed Goes Unpunished never looked so bleak...
Constance Hackett is a truly awful person when we finally meet her: She's one of the most foul-mouthed characters in the game, quick to berate her own son Travis when he informs her of Kaylee's death, perfectly willing to shoot Laura just for "being irritating," and downright cruel towards any werewolf outside of her family even though she should know full well they were most likely turned by her own son or one of her grandchildren. It's hard, then, to feel much sympathy if Laura wins the struggle for the gun and blasts the old woman to Kingdom Come... for Constance, at least. The moment the lights come back on, the entire rest of the human Hacketts are treated to the grisly sight of their matriarch dead and barely recognizable on the floor.
Travis' last interaction with his mother before this would have been hearing her scream at him for not just murdering two innocent people instead of keeping them alive long enough to escape and kill Kaylee, calling him a useless piece of shit multiple times along the way. The same mother who, along with the rest of the family Travis is desperately trying to protect in any way he can, died thinking he was worthless and just as much at fault for Kaylee's death as Laura. Travis will now never have the chance to mend his relationship with his mother; any possibility that Constance might eventually have come to regret the things she said to her son has just died with her.
Jedediah rushes to his wife and gently urges her to "wake up" while attempting to perform CPR, clearly in too much shock at first to accept that there's no saving his beloved Constance. He mumbles "Momma's gone, little Bobby," then stands up and tells Travis there'll be no more protecting people in an absolutely broken tone of voice. He may be unlikeable in his own right the few times he's encountered in the woods before this, but he clearly adored Constance, and now his last memory of her is the blasted ruin of her face.
It's hard to tell whether Bobby fully understands what's happened, though between Jed's comment and Bobby's clear mental handicap it's very likely that he doesn't. During the last few encounters in the house after this, Bobby never seems sad or even particularly shaken - he simply seems to be hunting Ryan through the house because that's what Jed wants him to do. If he survives the night, he will do so at the cost of his mother, his niece Kaylee, and his brother Chris, at the very least. Being one of the least openly antagonistic Hacketts throughout the game, it's hard not to recoil from the idea of poor Bobby now having to come to terms with losing three or more of his family, especially with his mother - probably one of his primary caretakers and/or emotional supports - being one of them.
The sheer fact that Chris Hackett and Ryan Erzahler are Mutually Exclusive Party Members, and one of them has to die for the other to survive the night. Ryan practically worships the ground Chris walks on, clearly seeing him as a Parental Substitute, and Chris seems to share the sentiment, interacting with him more like his own son than one of his seasonal employees. From the picture Chris keeps on his desk, it seems Kaylee and Caleb also consider Ryan a close friend if not honorary brother, and again Ryan shares the feeling judging by how devastated he sounds and looks when the group discover Kaylee's body later on during the night. If anybody deserves a happy bonus ending where they can meet up and reconcile with each other the next morning, surely it's Ryan and Chris - but when werewolf Chris breaks free near the end of the night, if Ryan doesn't put Chris down with silver, Chris will use the gun to cave Ryan's skull in. Either Ryan has to go on grieving his father figure and mentor, or Chris will wake up the next morning and have to face the reality of what he's done to Ryan.
Although Eliza was happy to exploit her son for profit and curse the Hacketts for trying to help him, and although numerous members of the Hackett family are shown to be relatively unlikeable individuals, ultimately the entire conflict between the Hacketts and Eliza can be traced back to two innocent mistakes: Kaylee and Caleb's decision to break Silas out without trying to discover why he was locked up to begin with, and their decision to use a fire as a distraction. Kaylee was only 15-16 at the time; Caleb was 20, and should have had more sense than to agree with the idea she came up with, but neither of them set out to hurt anyone and Caleb likely thought he could set a fire that would cause mayhem without getting out of control. A teenager and a young adult, making two very crucial mistakes that anyone could have made - and it resulted in property destruction, the deaths of multiple innocent people in the fire, and the spread of lycanthropy through the Hackett's Quarry area.
To dig it in harder, neither Eliza's curse not the Hacketts' increasingly misanthropic attempts to put an end to the curse can be considered entirely evil or without reason. Eliza is grieving - her son is alone and probably terrified, feral or no, and she can do nothing to help him. Of course she cursed the Hacketts: It's probably much easier to despise the entire family than to accept that the entire thing was a mistake. And the Hacketts are trying to protect their family and cure the ones who are infected, without involving outsiders if it can be helped. Yes, their methods are extreme and two or three of the eldest among them are entirely willing to hurt or kill innocents if it's easier, but they're terrified and desperate to end this nightmare, and thanks to Laura and Max we have clear proof that very few people, if any, would have believed them if they went asking for help.
Speaking of Eliza, regardless of how you feel about her and the things she's done, there's no denying the depth of her love for her Silas. Everything in the game is meant to fulfill her curse on the Hacketts for killing her and leaving her boy alone in a world where nobody else even knows what he's infected with, let alone how to help him. Even for a player determined to put Silas out of his misery and foil the Hag of Hackett's Quarry, it's difficult to walk into that final encounter with the White Wolf and not cringe as Eliza pleads more and more frantically for you to turn back and spare her son. She made her own mistakes and has her own fair share of personality issues, but she truly, genuinely loved that boy.
On the other end of it is Silas himself. As far as we know, he's entirely feral by the time the prologue starts; we do not, however, know for certain that he was always feral, or in fact anything at all about his mental state prior to the fire. We don't even know for certain how old he is; if he's slain, the shots of his human form seem to suggest he's in his teens or very early twenties, but there's no solid age given. What we do know is that he returns to the site of the fire even six years after the fact, even as a werewolf, and uses the burned out remnants of his old cage as a nest, and that paints a tragic picture. Regardless of how abusive or uncomfortable his life was before the fire, clearly he misses something about it now that he's alone... or, perhaps, he simply misses his mother, who we hear and see hauntings of most consistently in the woods around his nest. Does Silas even have the capacity to process his own grief?
