If you decide to use DOS (..16-bit real mode environment, not protected mode..), you may end up having to learn more about the x86 architecture then you intended.. if the coarse assumes a 32-bit environment has already been established.
Think of real mode like an early mode of operation that no other modern architecture has, other platforms supported by *BSD and Linux typically boot up directly into 32-bit or 64-bit modes.. something unheard of in the x86 world, so I would actually avoid learning about it and even opt for 32-bit assembly programming on OpenBSD as an alternative.
Instead of pulling your old i486 out of the attic(..do it anyway, OpenBSD will likely run on it), several emulators are available on OpenBSD.. consider QEMU, BOCHS or DOSBOX if you decided to go down that route.
Hope that helps..
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