Elmofongo: So I have installed a lot of old classics from GOG, but I tried to get a lot of them to a higher resolution because a lot of these older games never supported 1080p or other modern benefits.
I have updated and installed mods for a lot the games I have, but I am struggling with a select amount that I am gonna list and then explain. Games I've been struggling with:
KOTOR 1 and 2.
Quake 3
Serious Sam The First and Second Encounter
Return to Castle Wolfenstein
Red Faction 1 and 2
Star Wars Dark Forces 2 and Mysteries of the Sith expansion
Star Wars Jedi Outcast and Jedi Academy.
Legacy of Kain Blood Omen 2
Quake 3 I have made run in 1080p before by editing the Config File on Notepad, but it came with 2 issues, the FOV on the Gun model got way too closer and the cinematics are gone, with nothing but a Black Screen. I had this same problem with games using the Quake 3 engine being Serious Sam, Return to Castle Wolfenstein, and Jedi Outcast. As for Quake 3, I tried using ioQuake3 but for some reason i never got it to work.
KOTOR is one of the most challenging to get running at HD, I checked the methods and I got a bit stumped on what to do. There was an easier method and that's using Flawless Widescreen (which I use for both Bioshock games) but i read that using Flawless Widescreen on KOTOR 1 and 2 will cause a memory leak and make the saves corrupted and unusable. I never tested it myself just to avoid the issue.
Legacy of Kain Blood Omen 2 has this issue where if I try to get it running at 1080p, the game just crashes to desktop. THe highest resolution I can get it to without crashing is 720p.
And lastly, Dark Forces 2 has been a pain to get running at 1080p for me. This game is the oldest and most jank of the list. I tried using the recommended mods to get it working, but I never seem to get it working right.
So if anyone is willing to help out with at least some of the games, let me know.
The other problem w/ some games is - their Steam-versions get updated, but retail or GOG versions don't.
Sometimes vice versa's true also - where GOG gets an update and fix, yet Steam and/or retail versions doesn't (go see FO3 and FONV; and The Saboteur).
For RTCW - install IoRTCW source port, to get better resolutions support.
For Quake 3 - use IoQuake 3 source port, for better res' support.
For KOTOR 1+2 - Higher res' support for this and KOTOR 2 is on Steam. KOTOR 1 and 2 are derived from Aurora Engine (which powered NWN1). You might want to see if someone has made a mod to get the fixes from Steam to work w/ Non-Steam versions of the game.
A lot of those Aurora Engine games and Engines that became a fork of Aurora (and derived from Aurora and modified heavily) have issues. Often, you'd need to run in Windowed mode first and then switch it with Alt-Enter (while it's open) to Fullscreen; and then switch it back to Windowed BEFORE you close it out.
Also, if need be - DXVoodoo or any DX Wrappers could help, for older titles. Especially DX9.0 and older DirectX games. You might be able to do things like run it at game's top res' in-game but then you can configure DXVoodoo (or another wrapper) either scale it or force it to a higher resolution, if need be; especially if you are trying to keep the UI at a nice size that you can actually read. You might lose some performance w/ a DX wrapper like DGVoodoo, but you'll likely eliminate a lot of other problems that don't get along w/ newer OS's and newer DX versions.
Make sure you also have some Widescreen and Fullscreen programs that can manipulate the game to another res', to scale it, stretch it to full-screen, or whatever...if need be. Sometimes, those can be the solution to stop a game from not booting, or flipping back and forth b/t full and windowed on its own, or other madness.
EDIT:
That's what I get for not reading the replies. Look like most have the answers for your already. AWESOME.