Some obscure title will surely have weird driver, hardware and OS quirks. For example Crazy Machines 2's physics break down and the fixes didn't work for me. They use PhysX for their physics engine, before Nvidia acquired it, and it was heavily updated of course and now the puzzles don't work anymore. Maybe somebody found another solution to it by now, but I haven't checked it.
Child of light, a Ubisoft game, I couldn't get working on windows 10. Forums say it hasn't been patched since vista... Even if I copy the files over locally I don't think I'll have much luck getting uplay to run. Thanks DRM.