I don't think I have ever played a Silent Hill to full completion. I might look for the time to go through all the games sometime. I'd plan on playing them in release order, but if someone has a better suggestion as to how they should be played, I'd like to know.
I really like Silent Hill. My favorite is Silent Hill 2. I don't not like any of them really. The universe and lore of the franchise interest me as a whole so I'm always ready to play another Silent Hill game.
It used to be my favorite game franchise, and I still hold SH1-4 in high regard. I have probably played the first four games over twenty times each, probably more for the latter three. I first got into the series in 2003 and since then I've completely immersed myself into its universe.
I think there is truly something unique about Silent Hill which cannot be find in any other video game series. While each game has its own distinct style, there's always some sort of dreamy, surreal atmosphere looming over them. Much of this is of course thanks to the amazing sound design. My favorites are SH1 and SH4 because of their incredible stories. SH2 and SH3 are great too though, and SH3 is probably the funniest one to replay but its story is the weakest of the bunch.
Sadly, everything went downhill with the release of Origins. Since then, the series has been stuck in a creative blockage that has developers obsessed with copying SH2 over and over again, as well as reusing the same type of aestethics, monsters, and plots. The series saw a small resurgence with P.T. and Silent Hills but we all know how that one turned out, lol. Nowadays, Silent Hill is truly dead to me and I've lost all sense of hope in Konami.
I have played SH1-SH:Homecoming and loved them all even though I never finished Homecoming.
I love SH2 and SH3, but I have the give SH3 the edge because the art direction in that game is still unbeatable to this day. Every room and location is memorable and has some sort of creepy detail that makes me shiver.
Also, I have to give love to SH: ****tered Memories. That game was addictive to play over and over even if it gets predictable once you have played it more than once. The twist in that game is UNBELIEVABLY good.
I played and own the first three games. I still think the best one was Silent Hill 1 - it had the most disturbing atmosphere (especially if you played the Japanese version with those knife-carrying deformed dwarves), although the plot was a bit too convoluted. Also, back in '99 it really stood out because it was the polar opposite of Resident Evil - but back then devs actually were after the games their competitors were not making...those were glorious days indeed. Everyone's crazy about SH2, which became the face of the franchise even though it was more of a spin-off than a real sequel (kinda like RE4 or RE7): I am not bashing it, but I never found it as scary as SH1. It did tackle more mature themes, but it never really unnerve me. Pyramid Head still casts a long shadow on the horror genre though: enemies like the Executioner from RE5 or the Butcher from The Evil Within are just its clones. SH3 is the best-looking horror game on PS2 (it kind of shows what a real, triple-A RE game would've looked like on the system) and I liked that it was a continuation of SH1, although not as disturbing. If I had to rate them, I'd say
1) Silent Hill 1
2) Silent Hill 3
3) Silent Hill 2
I wasn't intrigued by SH4: The Room and I never bothered with the following games (which are not very good, as far as I know - they are like the STV Hellraiser sequels). I wouldn't mind seeing a remake of one of the first three games or, even better, a new sequel made by a reformed Team Silent...I never got to play PT (I didn't have a PS4 back then), but, from what I've seen, it didn't really feel like Silent Hill. Also, first person feels even more wrong with SH, given how cinematic the series has always been.
I've only seen the first movie in full (I didn't make it past the first third on the second one) and it was bad imho...even though it was a whole different game than the RE movies: the look was spot on most of the time, but everything else felt out of place.