Wishbone: I bought a Silent Hill game once, just to see what all the fuss was about. It was extremely weird and extremely boring. I think I played it for about an hour, then uninstalled it. It was The Room, by the way.
I've also seen the movie. The whole thing screamed "Console game!". Also very weird and very boring.
To be quite honest The Room is definitely not the best choice for an entry into the series, but if you ever decide to take another stab at it try to get your hands on SH2, it's largely considered the best of the series.
As for Konami joining GOG, I wouldn't hesitate for a second to get nice DRM-free installers for my beloved Silent Hill series, however Konami doesn't seem to care that much about the PC gaming audience and largely releases for nothing but consoles nowadays. I'm not holding my breath.