I've always admired the Silent Hill series from afar (or rather, the first 3), but I've never really played them. From what I've read, the second game is the best of the bunch, so I was thinking of giving it a go. Is it still enjoyable? I've heard murmurs about the HD collection being a bad way to play the game, so would you guys recommend finding a PS2 copy? I tried emulating it on my PC a while ago, but to no success. So it'd either be the HD Collection or finding a used PS2 copy.

Just grab the HD Collection. the SH2 port is pretty good. It's the SH3 HD port that suffers.

Also yeah, SH2 is always worth playing.

The HD collection is better on the PS3 as they patched that version, don't think they ever patched the 360 version, the voice actors they re-did for the HD collection are pretty good too, but I never had much of a problem with the original voices.
That being said, the HD version is horribly broken and even strips away some visual effects the PS2 version had, it was an atrociously terribly done version and I would avoid it at all costs.
The HD version is so terrible that Konami gave away free games to people who bought it as an apology, so, you know, keep that in mind. The biggest problems I had were when I was running around there was bad lag on the character animations and when the game loaded from the pause menu, inventory menu, cutscenes and building/door transitions the game would start up but for a few seconds the screen would remain black, allowing enemies to attack you before you gained your barrings.

However, as to if it's worth playing it or not, I would say it is, as long as you know what you are getting yourself into, old timey survival horror controls and inventory and what not. But if you are into that, it's great, it still holds up, the story is still awesome and self contained so no plot points need to be known about the first to make any sense out of it. I would say go for it, but the Silent Hill series is one of my favorites, so perhaps I am a tad biased.