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For me, if it were between selling a Boxster and having no fun car and no possibility of getting another fun car or keeping the Boxster, there would be no question (if you don't need the money or garage space). I have a little kid too and I know how hard it is to get time to hop into the fun car and go for a drive, but the opportunities do come up, and if I didn't have a fun car to take advantage, I'd be sad.
However, if this were an opportunity to explore the other sports car options, my answer is different. As great as the Boxster is, there are other fish in the sea. There are sports cars out there that offer a very different and in some ways better driving experience. Sometimes it's good to experience what else is out there and broaden the sports car experience.
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