Would I like Silent Hill?

[Fear Everlasting]

I would suggest, as an introduction you try Silent Hill 2 so the graphics don't make you woozy like SH1 (it's very dated, but SH2 graphics aren't badly dated because it was remade several times, the PC version has some bugs though), you get used to the tank controls, and it will embed the sense of false security you're going to want to fully experience Silent hill 1 and 3 which should be done afterwards.

Play Silent Hill 4 at least once for the experience, it's fresher than the other games due to the fact that combat was slightly made better and the cutscenes are fucking scary. It does have some light connections to Silent Hill 2 which you may or may not notice.

Avoid Silent Hill Homecoming and Origin. Homecoming is a fucking mess of a game with plotholes out the ass, a story made of pure shit, Resident Evil 4 combat that is retarded easy to exploit, and no emotional value. Along with how you get the endings can leave you really fucking confused if you end up with the UFO or Dog endings on your first playthrough (which is fucking easy to do). Origins is just some bullshit that gives about 20 seconds worth of backstory for Silent Hill 1 and horribly designed enemies and stories, in my opinion.

I haven't played Shattered Memories, but I heard not to think of it as a Silent Hill, otherwise you'll be disappointed.

To rephrase, I suggest playing Silent Hill 2 first, then Silent Hill 1 and 3, then 4 if you want some more, and avoid the rest like the plague.