Neat concept. Luckily I only know of one or two games from the win95 era that don't work in XP (mainly EA games like Need For Speed 3). As an aside, since the beginning of win2k and XP, people have said old DOS games can never work with these newer OSes.
Last weekend, a programmer (!!) friend of mine admitted to having never played Scorched Earth. This just couldn't be, so I dug up the old shareware and unzipped it. I ran the file and it ran perfectly...ok, mouse coordinates were off, but who needs the mouse? It WORKED! We played it for a couple hours. Good times.