Winter does not have a gambling addiction.
The motive is quite simple: the unfortunate bystander girl who was tragically shot by Naito was none other than his sister. He claims to be an only child now, but that's because he lost his only sister. His parents moved away because of the accident, which is why he now lives alone.
His purpose was, of course, to get revenge. Being a teacher, he knew Naito's sister attended that particular high school. And so, he decided to go after young schoolgirls of her age, killing them one by one, until he saw that his intended target had been assigned to the case. Then, he started leaving taunting messages, to further stress him out, before finally striking at his true target: Naito's sister.
However, a student who was well-liked, charismatic, and capable of getting the names of all of Chika's recent contacts?
The culprit is the final victim, Meruko.
Seguko (who she edits for) and Naito (her brother), are absolutely obsessed with murders. Furthermore, Seguko is obsessed with the works of Masahiro Junsuke, and Meruko is the only girl in his life, to the point where he mentally conflates her with the doll-victims of [The Smiles of Heaven]. Based on his writing and subtle cues, she is aware of this.
While in theory her school interactions might give her a respite from this environment, Masahiro Junsuke and serial murders even come up there, as Clair pushes his books at her. This leads to an obsession.
Eventually, she found out - or perhaps merely started to believe - that her mother was Masahiro Junsuke's wife, and that she was the child of infidelity whose existence led to Masahiro's bleak writing. She formed a fantasy in which she was the controlling narrator of [The Smiles of Heaven], making girls smile.
She chose victims to match her age. The "Mom, Dad" lines in [The Smiles of Heaven] suggested that the killer in that story was young, too, and killed "friends."
The "Mr. Detective" notes were an added flourish to get her brother's attention, based on when she heard Winter use the term; it was both a blind and a taunt, meant to deflect attention towards Winter.
In the end, she even did what the narrator of [The Smiles of Heaven] was implied to have done... and cut a smile into her own face.
Signature 1: A girl is killed who lost a close relative in the war. She is cheerful and popular.
Signature 2: A girl is killed who did not lose any relatives in the war. Whether she is popular is irrelevant. However, a taunting message is left on the body for the detective.
Two signatures mean two killers by the story's logic.
The first killer was Akari Junchiro, who was a huge fan of the novelist Masahiro Junsuke. She envied the popular girls and wanted to be the 'hero', or protagonist. She modeled the killings after the book [The Smiles of Heaven].
The second killer was Entror. He took advantage of the fact that he had a clear alibi for the first set of killings, and imitated their MO to begin a cat-and-mouse game with the detectives, figuring that he was above suspicion. He heard Winter use the term "Mr. Detective," and put that in the notes as a blind. His goal is to prove his superiority.
Either way, the love of risks and gambles was a major part of Killer Two's motivation -- the chance to play a game for major stakes.
The second killer is Winter, with the signature of killing girls who take care of their brother. He is a fan of Seguko... and so he is a fan of Masahiro Junsuke, because they are the same person! Seguko speaks of Junsuke like he is a different person because he feels detached from him, as if when he writes as Junsuke he's on a whole different level, and not himself.
Winter followed [The Smiles of Heaven] as well, seeing if Naito would smile in the end, after all that happened (that's the reason for the mockery), as the protagonist of the novel did.
Seguko is the second culprit, and he is Junsuke as well. His narration during the fourth and fifth murder is very detached, so he may very well have killed them. He killed Meruko and didn't remember it because of the hangover, maybe he thought he had killed someone else. Seguko may be aware when he becomes Junsuke, or he may not be.
The motive is he wants to reenact what happened in [The Smiles of Heaven], and see if Naito will smile. The second signature is "girls who live with their brother".
Killer 2: Winter. Effectively, this is Fedemon's theory with a different culprit. He once had a sister, who was shot in Naito's gunfight. He is subjecting other people to the loss he felt and getting revenge on Naito.
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Smile For Me
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The first killer is Akari, who killed the first three victims with the signature of the popular girl who lost a relative in the war. The motive was she was inspired by [The Smiles of Heaven].
The second killer is Winter, with the signature of killing girls who take care of their brother. He is a fan of Seguko... and so he is a fan of Masahiro Junsuke, because they are the same person! Seguko speaks of Junsuke like he is a different person because he feels detached from him, as if when he writes as Junsuke he's on a whole different level, and not himself.
Winter followed [The Smiles of Heaven] as well, seeing if Naito would smile in the end, after all that happened (that's the reason for the mockery), as the protagonist of the novel did. -
Winter never read [The Smiles of Heaven]!
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Same theory as above, but Leraz is the second culprit, and Leraz is also Junsuke's child (perhaps Seguko's), since Junsuke and his wife had an argument. So Leraz followed his father's steps and reenacted [The Smiles of Heaven].
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Leraz is not Junsuke's child.
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The first killer is Akari, who killed the first three victims with the signature of the popular girl who lost a relative in the war. The motive was she was inspired by [The Smiles of Heaven].
Seguko is the second culprit, and he is Junsuke as well. His narration during the fourth and fifth murder is very detached, so he may very well have killed them. He killed Meruko and didn't remember it because of the hangover, maybe he thought he had killed someone else. Seguko may be aware when he becomes Junsuke, or he may not be.
The motive is he wants to reenact what happened in [The Smiles of Heaven], and see if Naito will smile. The second signature is "girls who live with their brother". -
Seguko didn't kill anyone. His alibi is rock solid too!
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Killer 1: Akari Junchiro. Signature and motive as I gave before.
Killer 2: Winter. Effectively, this is Fedemon's theory with a different culprit. He once had a sister, who was shot in Naito's gunfight. He is subjecting other people to the loss he felt and getting revenge on Naito. -
Winter never had a sister!
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As above, but Federick is the second culprit. His sister or stepsister, who married into another family, is the woman who was shot.
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Correct.