My opinion..
Silent Hill 2 ≥ Silent Hill 3 > Silent Hill 1
....the games that came after these three just weren't in the same caliber imo.
Silent Hill 2 is the most highly regarded overall, but then again, that's because much more people have played SH2 in comparison to SH1 or SH3, mainly because SH2 is it's own self contained story, while SH1 and SH3 are directly connected. Also, SH2 was more widely available on a greater variety of platforms - SH1 and SH3 never came to the original Xbox.
A little advice....if you plan on playing SH3, you'll want to get the either the Good or Good+ ending in SH1 in order for SH3 to make sense.....since SH3 continues off either of the "Good" branch of endings. You can find out how to get the Good+ or Good ending on the web, it involves using a bottle to get a liquid at the hospital and most importantly, finding a secret in a motorcycle at the hotel in the Resort area.
Anyway, Silent Hill 2 is regarded as having the best story, but again, that's because it is it's own self contained story and like I said, more people seem to have only played that one. The overall story in SH1 and SH3 is just as good as SH2, that is, when you take into account that SH3 is a really great continuation of the storyline of the original.
Silent Hill 2 is the smarter game in terms of using mature themes......but it loses to Silent Hill 1 and Silent Hill 3 in terms of being scary. Silent Hill 2 was more disturbing or creepy rather then being actually scary the way SH1 and SH3 was, mainly because SH2 didn't have the dark other-world featured in SH1 and SH3.
Silent Hill 3 has hands down the best graphics and visual presentation of the series, It also has hands down the best protagonist in the series, made even better cause there is a cool twist on her real identity, which you discover mid-way through the game which was a great service to fans. I would also definitely say SH3 has the better voice acting out of the original Team Silent developed titles (I hope you're playing the original versions and not the horribly botched HD Collection).
Anyway, here's my personal breakdown:
Scariest: Silent Hill 1 - with SH3 as a 2nd place runner-up.
Best Story: Silent Hill 2 - with SH3 as a 2nd place runner-up (considering you got the Good+ / Good ending in SH1).
Favorite Protagonist: Silent Hill 3
Best Antagonist: Silent Hill 2's Pyramid Head.
Best Graphics and Sound: Silent Hill 3 - Hands down.
Best Voice Acting: Silent Hill 3
I should also note that some fans consider SH1 - SH3 to be the true Silent Hill series. The first three games had consistent positive acclaim, going by Metacritic the first three games score in the mid-to-upper 80's range.
http://www.metacritic.com/search/all/silent+hill/results?sort=score
After the first three games, the series had a noticeable drop in critical reception, and the series just kept going down.
But also, mainly because Silent Hill, Silent Hill 2 and Silent Hill 3 are the only games that Hiroyuki Owaku and Masahiro Ito worked directly on, who are considered the two most important people throughout Team Silent's existence. Owaku was the co-writer of SH1 and the main writer of the story of SH2 and SH3. Masahiro Ito designed the series signature look and signature monsters, such as Pyramid head, pretty much the whole visual style of the original games - they both left after Silent Hill 3. So even though "Team Silent" is credited with SH4, the two of it's most important members weren't involved with SH4's development. Also, the ending of Silent Hill 3 can pretty much be seen as a proper conclusion to the core original Silent Hill storyline that encompassed SH1, SH2 and SH3.
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