I used to drive my 911 year ‘round here in CO. It’s all about tires. The Boxster would be great. I have a Jeep so I don’t need to drive mine in the winter nasty. But, we do get plenty of cold but nice days, and the car comes out any chance I get. Honestly, I don’t drive mine in the nasty conditions because I’m lazy and don’t really like to wash my car. So, I drive it on the shiny days. Fortunately, we have plenty of them here.

The main issue I see is ground clearance, if there's more than 5-6" of snow you're going to start plowing with the front spoiler. Not to mention the damage an icy chunk or ridge could do !

Under most circumstances with a good set of snow tires the 986 is a perfectly capable winter car. It's at least the same as any 2WD sedan or coupe with snow tires, which is to say pretty good on plowed to lightly covered roads.