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I have a 2001 Boxster S and my wife has a 2008 Cayman S. I have a hardtop and winter tires for the Boxster and it goes just fine in the winter. Even though I have a set of winter tires for the Cayman, I laid it up this past winter. The previous winter we only drove it a couple of times, and not in the snow. The bottom line, as far as I am concerned, is to get a hardtop and snow tires for the Boxster. I think it's more fun to drive than the Cayman anyway and you are not going to make it worth any less money by driving it in the winter.
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