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I'm in the sell the bike camp. I'm thinking about selling mine because I always grab the box key first. I do like to drive with the bikes though. Certainly a lot safer too. Your wife can and will enjoy riding with you. And if you live in an area with a helmet law...
I would say go with the S, although I must admit I never drove a base. I just feel there is a little more there to run with the faster cars and bikes. And with the machines you have been driving...
I think the box would make a fine DD as long as there is not a lot of traffic or stop and go. The Boxster loves to be exercised. And, I use mine to do restrained Costco runs all the time. It is amazing what you can fit in.
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