My favorite part about running a ten year old game is getting "can't initialize D3D" error messages, and then have the internet explain, "bro, you need to update your drivers. That's how the game talks to the GPU. Few understand this." Yeah, bro, my week old drivers are too old to run a ten year game. I'm sure you've nailed the problem.
Spoiler alert, drivers were not the problem.

Basically the game does this at start up:

if (fullscreen)
    context = createFullScreen();
if (windowed)
    context = createWindowed();
if (!context)
    dieHorribly();

After you've run the game and created a settings file, it works. When there's a new install, there's no settings for either option, and no context created.

How this ever worked, or whether it was somehow broken in a later update, remains a bit of a mystery, but that's how it is.

@meena dig through enough forum posts, you can sometimes find somebody with a clue. Usually downvoted at the bottom.
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