Mhh DK2 runs fine for me on Vista x64 but only with modded drivers, for some reason these also made Crimson Skies not crash, but instead run slow as hell (or way too fast, in software)...
What we need is a true game machine emulator of the old days, Dos Box only emulates DOS to some extend and does not allow installation of Win 3.11 (which means all games of that time are unplayable, and theres NO emulator for it)
You can install W95/W98 in a VM but you won't get the needed gpu emulated. Most VM's use some weird as heck Rage (Ati) chip as Emulated GPU which didn't play 99% of the games back then.
Just saying
DK2 by itself also did not age well - i am stuck with 1024x768 res and the game is really ugly by todays standards... and nowadays you notice a lot of things lacking in the gameplay as well.