Maybe GoG could make DK2 work without too much trouble.
If I'm not mistaken, I remember that to get DK2 to stick on Software Acceleration, you need to deactivate it in the menu (usually, you can still see the text itself, even if the rest turns black), then, without quitting the game, launch a single player campaign. Then save, exit and quit the game. This way, DK2 should keep your full settings. Then it's true than by default, software is limited, but add -softwarefilter -32biteverything to the shortcut target and it should look very close to hardware acceleration (maybe with strange lines around textures, try without one of the command lines above). Still, the game may crash. Maybe lowering resolution or playing with compatibility parameters would help.
I've not played much on DK2, but I can definitly say that it's a bit slower and less impressive atmosphere-wise (the music is less striking, and sfx are a tad lower) - it does add some very interesting options and a more complete interface though, and skirmish as a native option. And silly cutscenes!