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Re:Show HN: A simple Unix-like operating system that runs Doom by ozkl on Saturday September 07, 2019 @11:29AM (#20904365)
Thanks! I was going to go similar path you mentioned. Not 16-bit but in a way that is exe-like binaries and development with Visual Studio.

But it seemed to me that it is easier to support ELF binaries. And OSDev has great articles about elf files, binutils, cross-compilers, etc..

Re:Show HN: A simple Unix-like operating system that runs Doom by mysterydip on Saturday September 07, 2019 @11:59AM (#20904589)
can't believe I never checked OSDev before... what a trove of info! I'll spend a while digesting there, thanks!
Re:Show HN: A simple Unix-like operating system that runs Doom by unixhero on Saturday September 07, 2019 @12:20PM (#20904730)
And deeper down the rabbithole: http://wikichip.org