Ok, I think we can now safely conclude that the original Machines Wired for War is definitely not future-proof. For anyone who may not have seen it, I believe that the creator of the Machinima series "Freeman's Mind" released an episode of his "Game Dungeon" covering a game called Dungeon Siege. In the episode, one of the most important quotes early on that came to mind on this topic was:
"This is another one of those weird games where a system from ten years ago runs it better than a modern one does today... Stuff like this is why I always get paranoid about changing an OS. This sort of thing ALWAYS happens with a new operating system. Sometimes there are fixes, sometimes you're screwed. It's also why I sometimes feel like punching people who think NEW software is always better. Doesn't matter what it breaks; it's new!"
Link to the video: https://www.youtube.com/watch?v=kgsR3qZp3-M
So yeah, it looks like I'm hyped for OpenMachines as that will bring the compatibility back to Windows 10, instead of waiting for it to arrive. Regardless, I'm sticking with windows 7 for a while.