I regret skipping Silent Hill 2. I played through the first Silent Hill when it originally launched, and I loved it. For whatever reason, I could never find the time to jump into the sequel, which I most often hear is the best entry in the series.
Also, it is great to see Konami making Silent Hill games again, I wasn't expecting a SH2 remake to be announced. I hope this works out well for them and encourages them to keep their incredible legacy alive in the modern era.