There is a known issue with Sierra which will cause D:OS Classic to crash on startup. The Enhanced Edition should work (but Classic saves are not compatible).
If you can not revert to El Capitan, can you use Windows in bootcamp? The Steam and GOG releases contain the Windows and OSX versions (and Linux for the EE); the App Store release is OSX only.
For the EE:
Are you shutting down all non-essential programs (especially anti-virus) before starting the game? Firewalls have caused conflicts (generally on startup or loading screens) and overlays from graphics tweaking/monitoring programs or chat programs have also caused issues.
Game Center has caused startup crashes (particularly in El Capitan).
Check for updated graphics drivers, etc.
Try pressing the Cmd key at game startup, and enable all the workarounds after, if possible.