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If you want a boost for DOS' compatibility under Windows XP, borrow the NTVDM DLL from ReactOS to perfectly play, for instance, Monkey Island.

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At that point just use any of the DOSBox variants. DOSBox Pure made for libretro is the best imo (as far as gaming is your concern) https://github.com/schellingb/dosbox-pure

Or just use ScummVM if Monkey Island (and alike) is your only goal https://www.scummvm.org/

I still like the idea of having it tightly integrated with the OS. Just double-click the EXE and it works.

Yep, I'd like soemthing like that for all emulatable systems.

Windows from such a systems could be seamless, and where possible access to the local fileystem + cut / copy /paste too.

Amusingly enough back in the day this is what it was with 16-bit, OS/2 and UNIX binaries

Monkey Island was just an example. OFC I know ScummVM (now it supports even some Macromedia Director based software). But lots of legacy software for DOS/Win 3.1 (these infamous "Multimedia CD's) could be preserved thanks to that.

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