Okay, first to the emulation question-
Provided you have a good, fast system, you can currently emulate anything out there except for 360, PS3, and PSP (If anyone knows of a good emu for those, let me know) The number one issue is finding a GOOD rom file. Many of the problems you'll encounter can be traced back to a crappy rom, just like many issues with ISO games is based off of a bad rip. So make sure you have a couple different sources to d/l from. Otherwise, as said, you shouldn't need too much time to get an emu up and running, especially the older systems. I've run almost every PS1 game perfectly out of the gate on PSX, and it looks pretty damned good. If you want to get started with emus and roms, head to another torrent site and just search for "emulator." Should be a couple 5-6 gb torrents that have EVERY game ever made for everything up to PS1 or so, along with emus and instructions. Plus, there's plenty of forums available for help if you get stuck, which I don't see as a problem provided a) you're at least somewhat tech-savy, and b) you're not trying to get MAME working (whole other bag of transistors there...)
Personally, if a game is out of print, I see no reason NOT to run it as an emulator. The only people losing money are the scalpers trying to rip me for $100 for a "rare, collectors item" that I just wan to fucking play. Not put away in a museum case in my basement, but to actually play. (I'm looking at you, Tactics Ogre...)