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Since it is going to be a weekend car, get the S. Just know that the less Boxsters are driven the more problems they tend to have (They don't like sitting in storage).
I would personally vote in favor of lower mileage, because you will get more life out of the car. You need to find middle ground between the year, mileage, and how you intend to use you. I would be look for an '03 S with about 30-35K miles, there are plenty of deals to be found in this economy. It's a buyers market.
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1999 Ocean Blue Metallic Boxster - blueboxster.com
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