The only problems I've had with this game are:
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When you install it, skip the tests. (You have to do the same thing with Windows XP, or any of the newer computers; it's an "old game" issue, not a Crossover issue.) Don't worry, you can run it, but the tests will crash the bottle.
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Mac OS X sees a disk being used by Crossover as busy, and won't eject it, so you can't put in the next disk when it's needed. Fortunately, there's a way around this: just copy all the files off the disk into a folder on your computer, then open winecfg for the bottle and tell it that folder is the D: drive.
Works like a charm! The game runs better on my Mac with Crossover than on my Windows XP desktop!