When hitting Start Game, a message pops up saying that it needs to update my DirectX version. After hitting "Continue" it tells me to "please insert Disc 1" but obviously, I downloaded this game. Wtf.

Have the exact same problem on a Windows 10 with new Creators Edition update

Have same problem

I had the same issue after reinstall windows 10. goto control panel. the click programs after that click turn windows feature on or off. You need to go down to legacy componets and enable directplay then allow it to do what it need to do. that fix it for me

Themaster123 is correct, after installing legacy windows components this game worked well