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Alessa Gillespie is based on a painting.
Namely, Andrew Wyeth's Christina's World. The house in the beginning cinematic is very similar, perhaps even a simple retouched detail of the picture. Christina Olsen, the subject of the picture, was nearly immobile due to an unknown form of muscular deterioration; Alessa Gillespie was crippled from her injuries in the fire and moved via wheelchair. Both Alessa's Silent Hill and the titular world are desolate and bleak.
The first game is just Harry Mason's Dying Dream.
Yeah, Jossed by the third, but it's one of the endings.
Cybil isn't Dead.
Like Harry, she went into hiding after the events of Silent Hill 1. The reason we never hear about her afterward is because she and Harry parted ways to maintain a lower profile. It isn't that she's dead, he's trying to protect her.
Both Alessa and Dahlia are Mages
from Mage: The Ascension. Dahlia is probably a Nephandus with the merit that links her avatar to the town itself. She's using Alessa as a channel to summon her lord, the Cult's God into this world. However, Alessa is also a mage, who sends her Avatar, Cheryl to try and retrieve help. The rest is history.
Leonard Wolfe is Alessa's father.
This ties into my other WMG about Dahlia being Claudia's mother. It makes all of them one big screwed-up family, and makes an extra layer of hell for Cheryl/Heather to escape from. As for why they didn't raise their children together, they could've had a falling out, or decided that God preferred for the children to never fully realize their connection.
Harry is descended from the Belmont family line
If he had the Vampire Killer, he could have destroyed the evil in Silent Hill for good. (Yes, this is a voice actor joke. Harry shares VAs with Richter Belmont in Castlevania: Symphony of the Night.)
Gillespie Coal and Iron Company
Dahlia lived on a received inheritance from "Gillespie Coal and Iron Company", but her instability and fire incident ruined her reputation and cost her most of her money from police and living. The stress is probably the reason for her evident rapid aging; her life has taken a karmic turn when she committed her crimes. It in no way managed to dissuade her from her plans.