https://bugs.winehq.org/show_bug.cgi?id=26715
--- Comment #10 from Serentty noname422@gmail.com --- (In reply to Dave from comment #9)
How about emulation of "real mode" within Wine itself? Maybe with the help of virtualisation (which will not cause performance issues)?
Emulation would overcome the hardware/kernel limitations and allow Wine to run many more Windows programs from the past, probably more than Windows 10 can.
This is something I would really like to look into. I would be willing to work on such a layer, but I worry that it wouldn't be accepted for merging due to the low demand. I think it's a real shame that Wine has near 100% coverage of Windows history, but is missing the first two versions.
Such a layer would also be useful for running Windows 3.1 programs in distributions that don't allow modifying the LDT.