Got some friends together to play through both Files and it's been a blast so far. If you like the old Resident Evils but never had a chance to play Outbreak online or if you did play it online and want to play it again I recommend checking out the fan server on a PS2 emulator.
I run out of shotgun ammo at around 0:30. Watch as I spend the next 20 seconds going to get some more but pick up the wrong box of ammo as I fiddle with the inventory 
I, uhh... kinda like Kevin since he's a very simple, noob-friendly character with his potshot ability, strong starting pistol, kick and good speed & health stats
. Is Jim the one he dislikes? I know the two of them have a funny special ending in the final scenario in File 1
I never really got into the game that much because it felt lacking as an offline experience. 20 years later I'm finally enjoying it in co-op, and I encourage you to give the Resurrection server a shot if you still want that itch scratched. You could probably have both File 1 and 2 running in less than an hour. The hardest part would be finding people to play with, though I think you can look for people on the Outbreak Resurrection forums and Discord. Maybe there's enough RE fans on Hexbear to get a game going
You of 20 years ago had good taste, the game is dreadful offline. It's a testament to how easy it is to love trash as a kid though, that I fell in love with it despite of that. All they had to do was remake the RPD in 3D, and kid-me was happy.
This post totally got me looking into that project and how I might be able to finally get that online experience in.
And it's actually Mark that Kevin dislikes. Kevin's a great character mechanically, I just think it's funny that those Japanese devs, either intentionally or not, painted a very realistic picture of these characters relationships...
Yoko's another great character for beginners. 8 inventory slots is a game changer in this game
To be honest, I don't think Kevin's a particularly realistic-feeling rendition of an American cop. He's way too friendly and laid back, and he reminds me more of Dante than your typical
, not that I'm complaining
Funnily enough, the two noobs in my group are Kevin and Yoko while the veteran is using characters like Jim and Alyssa.
If you're looking into setting up the games, this video's pretty good, but you can skip all the stuff about iso patching since CdRomance has the required English-patched Japanese isos ready to go. Honestly, waiting for the roms to download is probably the longest part in setting the game up:
https://www.youtube.com/watch?v=qFVibXHwP7A
I found a YouTube link in your comment. Here are links to the same video on alternative frontends that protect your privacy: