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I think it depends. If you're not apt to configuring Wine manually, and setting up Windows applications in Linux the manual way - then Crossover is worth the money as it will do everything for you with a few clicks.
One good example is at my old job, I set up Crossover office on desktops of people who were fairly new with Linux, so they could install and run Windows applications with ease. That was well worth the cost, as it cut down on people calling me and asking for help.
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