I finally got access to my sister's old Windows 2000 computer. Believe it or not, it's a Windows XP computer. Yes! If any computer is going to run Her Interactive's Vampire Diaries game (from 1996), this should be it!
I put in the game CDs, and they worked! I started installing the game, and...
The application is not supported by Windows NT.
What? No! Game, please work! I don't even know what a Windows NT is!
The official solution to the problem is to expand .dll files in the System32 folder, by using the original NT disc. I don't have that disc, and I tried checking Windows Update. This is the old version of Windows Update, which doesn't work unless you have the Microsoft website open in Internet Explorer.
No dice. It looks like I will NOT be able to play Vampire Diaries.
In other news, I have a Windows XP computer now! What are some classic games that I should get for it? I'm half-tempted to use it for speedrunning. Official speedrunning rules say that you can't use emulators, which is why you don't see official runs for famous games like Oregon Trail or Myst. In fact, the only Myst runs they have posted are for RealMyst, the 2000 remake. I could easily get the record, by virtue of being the only person using the original version!