I asked this question and was closed as too broad because of the statement that it would require upward hardware compatibility but which is wrong. (ᴡɪɴ9x still works natively on latest hardware with limit cpuid maximum enabled and ≤1Gb RAM) (linux 2.2.0 for PowerPC still works on qemu)
The problem lies with the bootloader (including with the installation medium) and this represent a narrowed scope.