Silent Hill 1/Headscratchers

Nope, no monsters here, everything's fine!

 * It's a minor thing, but the absence of any indication on Harry's part that he notices there are A. Monsters and B. a Dark World when talking to Cybil, Dahlia, and Lisa (okay, Lisa probably doesn't need convincing, and he likely won't bring it up so as not to upset her, but she at least wouldn't think he was crazy if he brought up the subject). Does Harry suffer from short term memory loss when switching to and from the Dark World, that makes him doubt what he saw? Or is he merely trying to seem sane to Cybil by keeping it quiet? I just think a lot of good paranoia mileage could be wrought from Harry trying to broach the subject progressively more to Cybil as she slowly freaks out at his potential insanity.
 * My guess is he is trying to appear sane to the nice police officer, she seems like the type to knock the crap out of him anyway if he told her that stuff up front.
 * In one cutscene, Harry mentions that his head goes fuzzy when he returns to the 'real' world, and he expresses doubts as to whether he is sane or not. Shortly before he enters the dark world via the chalice in the boutique, he does try to tell Cybil, but presumably feels foolish and gives up.
 * Harry does try to tell Cybil about the other world, as noted above, but she brushes him off by saying he's exhausted. The next time they meet, the otherworld's overtaking the town and she admits that he was right. As for the monsters, everyone he's met already knows about them. Kauffman has a monologue about them, and one of the first things Cybil says when they meet for the second time is "things are worse than I thought, this town is dangerous".

Writer Trumps Cop?

 * I'm fine with Cybil giving you (a civilian) her gun, given the circumstances, but why does she follow your lead, and generally act like a secondary character, when she's the trained professional, and you're some random guy?
 * Gameplay and Story Segregation?
 * Maybe Cybil only exists in Harry's imagination? Or because she believes in him? Or maybe cause he saw a cop pass him on a motorcycle, and made up a backstory so he could defend himself against the monsters. Isn't that how the Seal of Metatron works?
 * She originally wanted to take the lead, implying that at any cost that Harry should just shut up and wait in the diner. But as the game goes on and Harry makes more progress than her, she just accepts it as it comes and follows his lead.

Fear of the what tends to what now?

 * What exactly is the significance of the introductory line? Yeah, it's creepy, but it doesn't seem to mean anything.
 * It was an attempt to make some profound statement about people fearing death, but ended up sounding weird.
 * Also, this was the PS 1 era. Localizations weren't exactly the best at the time.

The military?

 * When Kaufmann and Harry are talking in Annie's Bar, Kaufmann says that a military squad is on the way to Silent Hill to rescue them. But no such squad ever shows up, and this is never mentioned again by Kaufmann, Harry, or the others. In addition, later games show no indication that the U.S. military checked the place out. So what's the deal? Was Kaufmann just lying to Harry? Granted, he's certainly not particularly trustworthy, but it doesn't make sense for him to just randomly tell Harry they were going to be rescued when they actually weren't.
 * Kaufmann was just guessing that a "military rescue squad" would be coming through sooner or later based on what he's seen of the town's condition. Even if the town really is cut off and devastated, that's a pretty generous assumption on his part (that'd still take a long while to happen, if it happens at all), but some of the later games seem to go with the idea that the town's not really in ruins at all, but the characters are all in another dimension.

The Magic Bullet?

 * In the first scene with Kaufmann, he shoots at harry at point-blank range and misses. But Harry didn't move until after the shot was fired, meaning that the bullet should've hit him. How did the bullet miss?
 * I think, PS 1 graphical limitations aside, Kaufmann was supposed to have jerked the gun away at the last second or aimed over Harry's shoulder once he realized Harry's not one of the monsters.