Good questions!

Tbh the only starting points I would recommend is the original or some version of sh2. Since it seems like this remake is really good I think it would be a great place to start!

Imo, the 2 S tier silent hill games are 2 and 3. However 3 is a direct sequel to 1 (an A tier game, only knocked down from S tier by PS1 jank) so i do think that should be played before 3.

The remake makes things a little different since it’s gameplay style will be pretty different, but my normal recommendation was:

Play 2 (PC enhanced edition preferably), if you enjoy that, then play 1 and 3. If you want more, play 4 (the last made by the original team and a good B tier game imo, but a bit different than the other 3). If you still want more, check out origins (a, imo, C tier game, the first made by not the original team but the most respectable effort of this new generation of games).

I’d say after that I personally don’t find any of them worth playing. Shattered memories isn’t my favorite but it definitely isn’t a bad game. I’d say play that again if you want! It’s more or less a very strange reimagining of sh1. An interesting game but not for me. A fine place to continue if you want more.

Homecoming and downpour are just quite bad imo. Stay away