Here's some "simple" answers user.
Play them in release order, 1-4.
Konami hasn't even bothered to rerelease any of the original games, not like anyone deserving would get your money anyway. You should easily be able to find any version of all 4 games anyway, PC or console, given how popular they are.
1 should be easily emulatable dues to being a PS1 game.
2's PC port is fine, but requires a little reworking to get running 100%. Plus there's no actual working mouse control in the game for some odd reason, but that doesn't affect much. The PC release is the Directors Cut version as well, so there's no reason to emulate it anyway.
3's PC port is perfect. It's been a while, but IIRC it requires some tweaking, other than that the only thing it lacks are some bonus outfits unlocked on subsequent playthroughs that are in the PS2 version, but not the PC due to copyright. No real loss there.
4's PC port is apparently garbage, I've never tried it because what little I played of 4 I didn't like, but it should be easily emulatable or there are fixes for the PC port.
If someone wants to post the big SHPC infograph that's be helpful.
Short answer, baka gaijin don't understand japanese horror.
Yes
The only post 4 game that's worth anything is Shattered Memories, which is more my personal opinion than anything. Everything else is just shit.
Really, the original dev team, Team Silent, split up after 4 and Konami passed the IP around to various western studios. These teams got very little input from ex-Team Silent members and what they did get from Konami or the fucking composer was counter to what made 1-4 good in almost every area. Every game, movie, comic, whatever aside from SH1-4 contain contradictions, misunderstandings and worst of all direct retcons of the source material and are best to be avoided outright.
Pay attention. SH1-4 are loaded with all the juicy, moist yummy stuff that makes a good horror game, and it's easy to miss things and get confused if you don't pay close attention, in that game itself and in the story. Also steer clear of the SHWiki if you want story-related answers, for reasons that I don't want to bother explaining.
Also Heather a qt, SH3 is the best SH, James is a faggot.