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I have a base (non-S) 2000 Boxster and love it. I personally like the looks of the 986 outside and inside better than the 987. I have had no mechanical problems. Like other members of the forum, I would definately purchase a car with a rear glass window. I added an aftermarket GAHH top with the glass window and have very pleased for about $1300. For the money you are willing to spend, I would purchased an S model for a bit more acceleration and some nicer electronics in the car. With the prices of used cars dropping, you should be able to purchase a nice car with a rear glass window for no more than $18,000. That way you can have extra money if and when repairs are needed.
Eric
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