Many of the great old games do work on modern PCs and can be purchased from Gog.com. I wouldn't blame Windows for the problems anyway the golden age of pc gaming was pre-Windows and getting games to run wasn't always a simple process and before everyone had internet there was a lot of trial and error on the way to learning. Many games that ran in earlier versions of Windows will still work on Windows there is a lot backwards compatibility built into it.
Anyway the DRM on Simcity is a totally different cock up I don't expect an 18 year old game to work on a new computer but if I wanted I could pick up an 18 year old computer for a vintage gaming rig. I have a modern computer and I can't play a modern game I legally bought because EA thinks I'm a crimminal so what is the true tradgedy?