There's certainly a cutoff period for this. Post-DOS and pre-Windows XP. I can't remember, but I think a lot of it occurred with games that relied on DirectX versions that came out before DX9.
XP broke a lot of DOS games because it wasn't based on DOS the way Win95, Win98, WinME were.
Then later on Win7 broke some XP games because MS went hard and heavy on restructuring device driver APIs for power management and security reasons based on XP being the massive success it was, and those two things becoming much more important than they were when XP came out.
DosboxX or PCEmu will often play stuff that requires Win98 or before.
For things that run on XP, I would recommend VMWare ESXi with your graphics card running through PCI passthrough. It doesn't handle 100% of all games (I've seen one or two that detect that combo as "cheating"), but it handles a lot.
My primary gaming rig runs ESXi with a bunch of VMs set up with various operatiing systems, and my graphics card is just old enough that I can find an old XP NVIDIA driver for a different card of the same architecture that works with it.
Virtual machines are becoming a necessity for retro gaming.
It's already been done somewhere and there must be guides for it.
There's certainly a cutoff period for this. Post-DOS and pre-Windows XP. I can't remember, but I think a lot of it occurred with games that relied on DirectX versions that came out before DX9.
XP broke a lot of DOS games because it wasn't based on DOS the way Win95, Win98, WinME were.
Then later on Win7 broke some XP games because MS went hard and heavy on restructuring device driver APIs for power management and security reasons based on XP being the massive success it was, and those two things becoming much more important than they were when XP came out.
DosboxX or PCEmu will often play stuff that requires Win98 or before.
For things that run on XP, I would recommend VMWare ESXi with your graphics card running through PCI passthrough. It doesn't handle 100% of all games (I've seen one or two that detect that combo as "cheating"), but it handles a lot.
My primary gaming rig runs ESXi with a bunch of VMs set up with various operatiing systems, and my graphics card is just old enough that I can find an old XP NVIDIA driver for a different card of the same architecture that works with it.