Patient Gamers

If you or anyone else is interested in playing more, I recommend:

• Silent Hill 2: Restless Dreams (aka Director's Cut). Not a continuation of the story of the first game, but a separate story in the same universe. Generally agreed to take everything good from the first game and improve upon it. The "Restless Dreams" version has a substantial extra scenario which adds some backstory and lore, but should probably be played only after completing the main game.
• Silent Hill 3. This one does continue the story of the first game, somewhat. To be honest I remember enjoying it but not much in terms of particulars.
• Silent Hill 4: The Room. Started out as a separate game unrelated to the Silent Hill mythos, but was rewritten to become an SH game during development. This sounds like it might be a terrible cash-in, but it really is a perfect fit for the SH universe. IMO almost as strong as SH2.
• Silent Hill: 0rigins. A PSP game set as a prequel to the first game. A little light on story, and with some odd combat mechanics, but I still found it very enjoyable. I played the later PS2 port.
• Silent Hill: Shattered Memories. A "reimagining" of the story from the first game. It plays and feels very different to the previous games, but I still enjoyed it quite a lot.
• Silent Hill: Orphan. A series of point-and-click adventures for Java-enabled mobile phones from the 2000s. Totally different mechanics from the mainline games, but they do the atmosphere and story well if you don't mind the slower pace of point-and-click. They run on some J2ME emulators.
• Silent Hill: Alchemilla. A free fan-game centered on the Alchemilla Hospital, but also including several other locations. First-person view with many puzzles and no combat. Very polished and really nails the atmosphere.

I played a little of Silent Hill: Homecoming but got tired of it about 1/3 of the way through (I guess). I also bought Silent Hill: Downpour but gave up on that even more quickly. I don't recommend either of them. Things introduced in the earlier games for specific psychological reasons related to the plot - especially sexy monster nurses and Pyramid Head - tend to be regurgitated in the later games for no real reason other than "Silent Hill", which removes their impact completely.