The easiest way is probably to use DXX-Rebirth. Basically it is a modern engine that uses the Descent assets. I played through both D1 and D2 not long ago using Rebirth on Windows 8.1 and everything worked great.
Might sound stupid, but have you tried to right click the .exe and set compatibility with win98 and run as admin?
Now if the game run in dos, all you need is http://www.dosbox.com/
The easiest way is probably to use DXX-Rebirth. Basically it is a modern engine that uses the Descent assets. I played through both D1 and D2 not long ago using Rebirth on Windows 8.1 and everything worked great.
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