I don't think you would be able to even install 98 on a sata drive running ahci.
apparently someone at some time had taken a VM and had upgraded through every literation of windows, and everything worked, even legacy software, tho vista and 7 killed the color settings from the original setup, other than that, everything was intact, so if the hardware was willing to run something for 20+ years, you could technically upgrade all the way to now, which is kinda evil
maybe someone should try this system of DOS to 7 upgrade on a system. Like build a cheap system and install DOS and upgrade to 2.0, 3.1 and so on till 7 to see if it works.
best of luck m8. lets us know how it turns out. (are you going ME to 2000 to XP, or skipping ME?)
apparently someone at some time had taken a VM and had upgraded through every literation of windows, and everything worked.
I saw that video, it was awesome.