In my experience, aside from DRM issues, it's the early 3D games from the late 90s and especially early oughts that run the worst : 3D acceleration is a pain to make to work correctly, and they are too resource hungry to be run well in emulation.
I my experience, Wine (+ dgVoodoo for some DX7/8 titles) runs these pretty well. There are exceptions of course but usually there is some way to make them work. Some also work fine in a Windows XP VM without any 3D acceleration.
