Not really a Vista problem.
Quote:
The harddrive the game is installed to has 20 gigs of free space.
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This. It's a common issue with early 90's games - if you provide them with too much free HDD space, when the game attempts to check the amount of available space the value won't fit into the type the game executable was programmed to use.
Put the game on a smaller partition, with significantly less space - 1-2 GB would be about right. Should work perfectly fine then.