My worst suspicion has been confirmed
I tried to install GTR2 on a stationary running Windows 7, and it would actually run the game, although slightly laggy (computer's fault). I then simply copied what I know knew was a working install over on my external hard drive, and tested it again just to make sure it could still run it, and once again it ran near-perfectly.
Then, I plugged the HD into my Windows 8 laptop..
Config Screen Of Death!
So it's pretty much confirmed that Windows 8 and GTR2 just don't like each other. Compatibility mode doesn't help either, you're still running Win8.
I'm wondering if installing Windows 7 on it would help, since the OS seems to be the main source of problems?