SOLVED: Your answer helped me find a working solution. However, my setup requires 2 additional programs to implement.
------------- REQUIRED SOFTWARE (+1): -------------
"WindowedBorderlessGaming" by Hellstrong:
http://forums.steamgames.com/forums/sho ... ?t=2675769
^ for making PlanetSide 2 windowed mode stretch to fullscreen (allowing "Always On Top" windows to actually be seen on top, instead of going "Fullscreen Windowed" in PlanetSide 2 where it jacks the "Always On Top" from all other programs and always stays on top.)
------------- REQUIRED SOFTWARE (+2): -------------
"See Through Windows" by MOBZystems:
http://seethroughwindows.codeplex.com/r ... view/71149
^ for click-through and transparency.
These are the programs:
------------- HOW TO DO IT: -------------
Step 1: Start Game, use OBS to capture in "Game Capture" mode. (Add an image/graphic/webcam/etc. to overlay on stream.)
Step 2: Open "WindowedBorderlessGaming" application (Note: Only applies to PlanetSide 2 and other games with oddball "Borderless Windowed Mode" or that lack a windowed mode. For PS2, you may want to move the task bar to another monitor.)
Step 3: Set to Borderless Windowed Mode, or configure WindowedBorderlessGaming to show your game in a *real* Borderless Windowed Mode. (For PS2, set to "Windowed" mode, NOT to "Fullscreen Windowed". That way it won't always stay on top.)
Step 4: Open "See Through Windows" application, configure hotkey, set to Opaque (or desired opacity), check "make window click-through" and "keep on top of other windows".
Step 5: Put OBS to fullscreen mode. Start the preview (with overlaid graphics).
Step 6: Move OBS window to same monitor (dual monitor setup) as game. You can do this with [Shift + Windows Key + Arrow Key] or just click + drag.
Step 7: Making sure that the OBS window is selected, hit your hotkey for "See Through Windows".
Step 8: Enjoy your game! (Also, make sure you are on the right window when you use hotkey for "See Through Windows".)
ENDING NOTE: This should work with just about ANY game, allowing you to "play OBS" in preview mode. This increases usefulness of OBS as you can use it to overlay just about ANYTHING on top of a "windowed mode" game window. (e.g. music players, Picture-in-Picture videos, facebook status updates, & anything else you can put on your desktop). It may even work for fullscreen games if you can use one of these programs to force to windowed mode.