Finally finished the game! Oh God, what a trip. Finally, a game that takes the spot from SH2 as my favorite Silent Hill game. Even with all the flaws and glitches, Climax did an amazing job. The immersion, the atmosphere (heck, there were parts that gave me goosebumps), the music... My personal best of 2009.
I think all the characters we see through the game, are actual people that Cheryl met. She met Cybil because she ended in the police station some times. Michelle was probably a friend in school, one that was quite successful in there. Dahlia was probably a school friend too, but more like a "bad influence" one. She probably met Lisa because she spent some time at the hospital. Each one plays a role for Harry according to what they did for Cheryl in her life. Cybil probably tried to help Cheryl, that's why she's like the only one that doesn't think Harry is crazy. Michelle was probably a good friend for Cheryl, that's why she's the same with Harry. In my game, it was her boyfriend that broke up with her, because she loved the image she had of him, not the actual man, much like Cheryl loves her dead father. Dahlia was bad in Cheryl's life, she took photos of her naked, probably influenced her to have an affair with a teacher, and probably got her into a "bad" job (see that... house). That's why she uses her as the image of her mother, probably blaming her for Harry's death, ie, making him to get away from her daughter ("turn back Harry!")
I think all of Harry's adventure was Cheryl remembering her life, probably backwards, that's why it ends with the amusement park (ie, Cheryl's childhood) and it starts with the "girl in the woods" incident. I see the girl being Cheryl, she was probably raped, and again, blamed her mother about it. My therapist said things like "sex is death", so she probably has some trauma about it.
In the ending I got, Harry got into the room, and froze up after saying "I'll always be there". She left with her mother, forgiving her, and packed up her mementos, probably meaning Cheryl accepted the death of her father, but still remembering him.
Man, what a sick game.