SumerNivek,
Actually, I just downloaded WCs 1 and 2 from The Underdogs (they finally put it up in a file that doesn't become a broken mess when decompressed). For some reason the music doesn't work, and input from the keyboard is kinda flaky (can't hold down Tab and use arrow keys to change directions at the same time), but it more or less works, and I'm running XP.
Have you tried right clicking the WC2.exe file and setting it to Windows 95 compatibility mode?
Anyway, even with semi-working copies of WC1 and 2, it just doesn't work without the music.... Sigh, guess I'll have to bid on eBay after all, or get a really old computer and install the original copies (which might actually be cheaper...).
I found it a bit disconcerting that they added voices to the pilots in spaceflight for WC2. Shadow has this heavy accent now, and I'm not sure I like that. I never imagined her having one when I first played the game.