So far so good, starts in an almost fullscreen window, displays the Lion logo in glorious 256 colors, tries playing the SSI video, crashes to desktop. Stellar job on bringing this to modern machines. And the install CD is not even included, so I can fix it myself.

EDIT: throwing the ddraw.dll included to the curb, and adding dgVoodoo makes it at least playable. Guess that means at this point I'm paying for the files, because making it run is apparently now my job.

I had this as well, I had done what you did and tried dgVoodoo2 (it works but the inventory is wonky and very laggy) and also GOG's own ddraw.dll (and associated dxcfg files) borrowed from my installation of Star Trek Armada (this worked a lot better for me than dgVoodoo2).

At that point someone else mentioned that the ddraw.ini file that comes with the installed ddraw.dll has some weird values in it, I think it listed my resolution as 1920x1440? Anyways I went through that setting a few things to more sensible values (set it to 1920x1080, set a 60fps limit, think I set it to borderless windowed as well) and that works and doesn't crash anymore, although it does give a bit of a stutter on the SSI logo where it looks like it might crash but it passes after a second and starts the intro video.

With a fixed ini file, the installed ddraw.dll and the GOG ddraw.dll borrowed from a different install behave about the same as each other and work pretty well. I think the defaults in that ini file don't like some display setups.

Interesting. What irks me the most is that you can't even try and take this deathkeep and run it on a system it was designed on, because they mucked about in the dk.dll as well, and if you try to run it on win 9x, it tells you to get a newer windows. This is not how preservation works.