[Overdrive]

I don't DD the Boxster year-round, just not realistic when it can turn into a snowplow if it snows too much. But when the weather's nice, I drive it as often as I can, and I couldn't care less if it rains. My car's not that precious that I obsess over whether or not it gets wet or dirty. I bought it so I could drive it.

You could simply use the company car and save miles on your 550 (there aren't too many of them out there, so that's one that's at least worth keeping out of the rain and taking care of). You can adjust your insurance due to the limited miles you'd be putting on the Boxster, save some money there, and you could even take it off the insurance temporarily during the winter if you know you won't be taking it anywhere. And I'd say don't take it for work if you're risking bringing it to poorly/non-paved areas or secluded places in the middle of nowhere where a tow truck will take half the day to find you if something decides to act up far from home.

If you ask me, if there's any car that should get the doghouse treatment out of the stable, it's the company car. Considering you just got the Boxster not too long ago, give yourself some time to enjoy it before you consider selling it. Take it to Lime Rock and/or autocross with the PCA and get some enjoyment out of what it can do besides look gorgeous.