TTripweed: I did some more looking into things.
I can run the NORMAL .exe fine.
It's when I run DK2 DX.exe where I start crashing.
Weird.
mikeycl: Just a quick thing to make sure of is that you have DirectPlay installed.
i had the same issues with these when i tried them on win 10 for the first time and it was because this is a deprecated and optional feature within windows (not installed by default).
You can install it via the Control Panel
For the control panel method go into Programs and Feature and clicking Turn windows features on and off. in there you'll find a section marked Legacy Components which when expanded will show DirectPlay as an available option. make sure this is checked and then click OK.
Windows will then go through the necessary actions to install the feature and once completed try loading the game again.