For whatever reason my brain has decided to think about this.
VLC will record the Desktop and Space Rangers but not Transformers: Devastation Though the game screen it captures for is a different size than what is captured with the Desktop while either game is running. Seeing what happens when Transformers runs results in a white screen being recorded while the game window is in focus.
My ancient Radeon graphics card and Windows 7 operating system (don't at me Linux folks, I know I know) has some screen recording stuff build into it. Will record the Desktop just fine, records only a black screen while the game is running and its window is focused for one game but records the other game just fine and at an appropriate size.
For curiosity's sake what would I be looking for as reasons or solutions to this?
Edit:
Running everything as Administrator seems to help in OBS. Who knew? 
OBS seems to play nice with Transformers: Devastation now, lets me draw the bounding box in the Game Source instead of trying to use the Display source.
Still haven't figured out why OBS is being wonky with Space Rangers not recording in "Game Source" but did get a lead on why the size is wonky in the recording of "Display Source". The max resolution for the CD version (the one I've got) is 1024x768 and my monitor is 1920x1080. (Unsure why there's a difference between what I see playing the game and what the software is recording.) And the only resolution patch I've found doesn't work on the CD version... :whomp-whomp:
So far, both my printers are working (one of which seemed to have been unable to work with my Windows installation after a while), I can get on the internet, and I figured out how to get my VPN running. I don't think I'll need to fully backslide. If something weird happens, I've got some crappy laptops that I can sacrifice as single purpose machines and leave my daily driver fully Linuxified.