I too live in Chicago and my 2000 Boxster S is my daily driver. Last winter I tried to drive my car during the first snow on the stock Michelins and I scared the hell out of myself. It felt like the roads had been greased. Then I equipped my car with a set of Dunlops (factory recommended Winter Sports)and the car was transformed. Although it isn't as good as my Audi A4 Quattro, it now starts, stops and corners extremely well on snow. I would tell anyone planning to drive their Boxster in the snow to get the same set up.
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Ray Vanderhulst
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