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I owned a '99 as my first Boxster. I made the mistake of not having at least all-seasons tires on the car even though the tread depth was fine. It didn't stop when I wanted it to. Totaled.
Tread compounds are as important as tread design. And wider tires are less good than narrower ones.
Grab a set of 16" Boxster wheels and put some legitimate snow tires on. Cheaper than trading a car in for something else.
I drove my second Boxster frequently in the snow.
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