Keep the Boxster because you wont be able to replace it (with kids thing always come up $)In a short 2-3 years you will be taking your kid for rides with the top down (great bonding with child)Buy a 2nd car for grocery getting and family stuff. The trick is to get something else you like to drive and can be proud of. I have a 04 MB E320 sedan. I put nice wheels/tires on it along with a 4 pipe exhaust system and an updated front grill. It rides great, looks great and has a giant trunk. They are expensive to get work done, but they can be bought pretty cheap. Now when I want to drive sporty I have the Boxster and when all the family drives together I ride the quiet, comfortable, yet sporty MB..........Its the best of both worlds.