I would like to thank everyone for contributing. There are way too many approaches to try them all, but my further research led me to the following conclusion:

I would like to thank everyone for contributing. There are way too many approaches to try them all, but my further research led me to the following conclusion: I'm going to start with trying Windows XP on either VMWare Player or qemu Most versatile / reliable source for Windows XP isos here[1] (needs registration) Trying this[2] modern installer creation may be a next step If this does not work, I'll try Win 98 SE on dosbox-x following this[3] guide [1]: https://forums.mydigitallife.net/threads/microsoft-windows-xp-iso-svf.44702/ https://forums.mydigitallife.net/threads/microsoft-windows-x... [2]: https://forums.mydigitallife.net/threads/tool-xp2esd-create-modern-windows-xp-installer-v1-6-2.82935/ https://forums.mydigitallife.net/threads/tool-xp2esd-create-... [3]: https://dosbox-x.com/wiki/Guide%3AInstalling-Windows-98 https://dosbox-x.com/wiki/Guide%3AInstalling-Windows-98