I'm wrapping up my 1-4 replay at the moment. All four stood up fairly well, as apparently did my opinions on them. Uncontroversial as they may be, here are some short summaries:
SH1: a really strong start for the series, especially sound and high concept stuff. Best otherworld structurally: a spectrum instead of regular+bad world that the series eventually settled in on. Monsters are kinda tame, relatively speaking at least.
SH2: best characters, best "straightforward" story. Great job at taking SH1 elements - fog, reality shifts, monsters etc - and putting them in a different context. Best exploration. Bizarre balance and difficulty curve.
SH3: most polished. Best otherworld visually, best enemies, best balance - just most pleasant to play overall, would recommend as the first one when getting into the series. Slightly too generous on save points.
Ridiculous puzzles on Hard.
SH4:
best trailers, possibly for anything ever. Sadly, that's about it for the good parts. Plays the worst, looks the worst, sounds the worst. Still captures its own unique weirdness once in a while. Goes to great length to make you feel uneasy, though I bet its gameplay ideas sounded better on paper.
For people who have never played a single one: Silent Hill games can be played in any order without losing much. All but the first one have PC versions, I've been posting notes on ports/emulation (
1 2 3 4).
I think it's time to release the Silent Hills (at least up to 4) on GOG.
Not gonna happen, thay had enough legal problems just re-releasing 2 & 3 for consoles, and that was back when Konami still cared just a tiny little bit.