I can't see why microsoft doesn't make a retro windows/dos OS system + modern lite browser + floppy drive emulator ect that will run on ARM for running old pre 2001 software and the Idea is that each year you get an extra year's compatibility.
A retro windows/dos device only needs to have 256mb ram and 64gb emc flash ram , 2 32 bit cores one extra for when browsing, to plug into hdmi and to emulate well 3dfx and up to direct x 8 or 9 and opengl 3 along with VESA vga ega cga tandy ect and with the cga mode it should mimic the wider color pallette some of to the games that were made for the right screen.You should also be able to buy old software for this range of retro devices.
Old software should be cheap as chips.