My question is this: Could Steam pick up Python and/or Oblivion and have that interfere with other Steam games? I know the VAC system runs the mod/plug-in checks all the way back to the directory in which the Valve folder is located and if the Valve folder is located outside of the Program Files folder, it can pick up foreign files and claim them to be mods/plug-ins. This is usually because nobody ever installs mods directly in their Program Files folder so it rarely ever happens. My old roommate had to move his Valve/Steam directory into his Program Files(x86) folder because Steam found some mods he installed directly to his My Documents folder and prevented him from playing games.
If you guys need more information, it might take a bit as I'm communicating with him via a message board. But I'll give updates as soon as I get them.