Most of the characters in Shattered Memories resemble their namesakes in the original. They have different personalities, but their roles are the same - Cybil's still a cop, Lisa's still a nurse, and so on. So why does Dahlia look like a piece of jailbait when the original was a creepy old woman? Then you get to the end and realize Dahlia represents Cheryl's mental image of her own mother. So she DOES fulfill a similar role to her original self. The designers did this deliberately to mess with people who have preconceived notions about Shattered Memories based on the original game; one said "We want people to look and say, 'Hey, that's not Dahlia!'"
During one of the therapy sessions, the player is asked by Dr. K to choose words that might have been used to describe them in high school. One of the words, "slut", is an unusual (albeit not unheard of) term with which to refer to a man. Most players will probably dismiss this as a quirk, until The Reveal at the end of the game.
In the spoof UFO ending James arrives at his couples counseling on the wrong day. Still having trouble remembering when significant things happen huh James?
The meanings of the mementos could probably have their own page in this. The best example would be the last two mementos you can find, two halves of a pendant. They have two pictures when formed, one of Harry, one of Dahlia. When put together, it reads "never forget true happiness" with the first two words on Harry's half and the last two on Dahlia's half. Remembering Kaufman's words at the end, this message could be for Cheryl, saying that she should not forget her deceased father but her still living mother is where she'll find the happiness she's looking for.
On top of that, the "Harry" half of the pendant is found inside a box in the shape of a head!
It took me quite a while to realize that you're not supposed to read it as "Never True" and "Forget Love". This duality between left-to-right then top-to-bottom versus top-to-bottom then left-to-right is probably intentional.
The nightmare world doesn't emerge at certain locations simply because that's where Harry uncovers an important plot point, but because those were places where Cheryl experienced great suffering!
The part of town near the road shifts because that's where her father crashed and died.
The woods shift because she went to a bad party there where she got drugged up and started stripping.
The school shifts because she was intensely bullied and abused there, even becoming a subject of gossip.
The bridge shifts because she probably went there, suicidal, and considered jumping off.
The hospital shifts due to her most likely being sent there after the crash to make sure she was alright, all the while being completely traumatized from her father's death.
IIRC, Cheryl wasn't in the car when Harry died. This still fits because she went there after she cut her foot at the cabin, an event where Harry died not long afterward.
The mall shifts because that's where she was caught shoplifting multiple times, and eventually stabbed a guard.
The pawn shop and accompanying home shifts because that's where Cheryl and her mother live, and it's OBVIOUSLY not a happy place.
The last nightmare chase, where the raw shocks try harder than ever to stop you, is on your way to the Lighthouse Clinic because it's closest to Cheryl and the trauma of her memories being shattered!
Another explination been put forth is that the Nightmare Sequences are Cheryl's way for keeping Harry away. If Harry arrvied, she'd realize the truth. It's her way of keeping him, the REAL him, away from her.
Was the girl who got drugged at the party supposed to be Cheryl? I thought it was implied in the second party echo that that girl died. ("We thought she was still swimming, but she wasn't moving.") Furthermore, that girl is referred to as "the new girl", while Cheryl has lived in Silent Hill her whole life.
This troper didn't realize this until watching an episode of NCIS, but static also has another term: "snow". Considering that static is heard as Rawshocks get nearer or just before the icy Otherworld emerges...
Dahlia appeared as though she didn't age all that well: in the "flirty" incarnation, for example, she grew to be an overweight, wrinkly old woman pathetically clinging to her youth by dressing like a tramp despite her age. Then you realise that it's how Cheryl, who hated her mother as a result of her guilt and twisted psyche, viewed Dahlia in her mind. If you meet the real Dahlia just before the credits roll, you'll see that she's... well, a video game-conventional mom.
Lisa...a NURSE, going home from a concussion, only to take some pills, and go to sleep. Stupid, particularly from a medical professional yes? When it's revealed it's all in Cheryl's Psyche, it makes a bit more sense. She gets the concussion from an automobile accident...like the one Harry died in. Perhaps her psyche's way of getting revenge on the person who should have saved her "Daddy?" At the very least, pretty good foreshadowing.
Another interpretation is that Lisa was the other driver in the accident which killed Harry, hence the significance of her crashed vehicle. Harry giving Lisa the wrong pill is a way of Cheryl's psyche seeking vengeance for her role in the accident itself.
When Harry and Cybil are at the diner, he doesn't realize that he has a cell phone in his pocket, and seems confused (but oddly accepting) of its presence. This makes sense, as Harry died in 1990, and a 90's phone probably wouldn't have been small enough to fit in his pocket.
The echoes about the man who slaps the prostitute in pigtails always seemed weird to me, because although I could see Cheryl turning to prostitution as a teenager, the scene itself feels strange and out of place, and we know Cheryl is capable of violence so it seemed odd that she'd let some john hit her. Then I realized: the girl he drives to school isn't Cheryl, it's the daughter he's sexually attracted to/may have sexually abused. That's why he flipped out about Cheryl not wearing pigtails: he's trying to indulge in a really taboo incest fantasy, something we already know she shares...
Whatever ending you get, Harry is wearing the same clothes that he wears in the intro, with Cheryl and Harry at the amusement park. That's why the tape in the opening rewinds before it gets to the end: it all happened that same day. In the "Love Lost" ending, we get to see the car, suggesting that Harry's fatal car crash happened shortly, perhaps immediately, after the tape was made. Of course Cheryl would fixate on that tape in particular. It was the last time she ever saw him alive.
In three of the endings, the camera angle suggests that Cheryl was the one doing the filming. In "Sleaze and Sirens", the camera is stable and probably sitting on a motel dresser or table; in other words, Harry's womanizing was taped over his daughter's happiest childhood moments. That may be the source of Cheryl's sexual interest in her father. Her most precious memory of him is inextricably linked with explicit images of her father having sex with women.
At first, Dr. K seems really unprofessional for a psychiatrist—why is he drinking on the job and keep bottles of alcohol in the office where he hosts his therapy sessions? But then The Reveal happens and we realize that all that we've seen so far is Cheryl being an Unreliable Narrator—the closest to how we get the "real" Dr. K is like is at the very end.
In the sinking car scene, the windows freeze over and the raw shocks scratch "Stop fighting", "It will all be over soon", and "So cold" into the frost on the windows. This implies that they very much dislike their current cold, icy situation. If this is so, why do they cower in fear as soon as Harry lights up a bright, warm emergency flare?
The way it was worded, it sounded more like the raw shocks were taunting Harry rather than expressing their distaste for the frozen atmosphere.
If not this, it's also possible that the monsters themselves are being tortured by Silent Hill. They're trying to absorb his body heat, after all.
Alternatively, have you ever been outside in below freezing temperatures only to come inside and try running your hands under a stream of hot water? The sensation isn't pleasant.
One way to think about this: Are the raw shocks talking to Harry? Or to Cheryl? Harry has been fighting to get in—Cheryl has been fighting to keep him out.
It could also be what remains of Cheryl's mental stability-she knows how screwed up she is and is begging to be let out of her Self-Inflicted Hell.