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I'm in the same position as you and I am shopping for Boxster #4. I can speak first hand of S envy when I bought my first one, a 99 base. Although I do not push the car to it's limits, I just like knowing I have the S version. I'm not terribly concerned with resale or 0-60 times but when I had the base I was always thinking of getting an S. Once I got my 01 S I never really thought about "upgrading." I really enjoyed the car, had zero issues and drove it as much as possible. Right now I am searching for the best bang for the buck and find myself looking at 986 cars. For me, I am looking 02-04. I Find the 04's too much $$ and only one year before the model change to 987. I like the 987's but can't justify the price difference between a 986 and 987 for how I am going to use the car. If I get a 986, 02/03 S and want to "upgrade" it will be next summer and the 987's will be a bit less money at that point. Sure I would love an 09 S but $46K doesn't work for me right now. I have a feeling an 02/03 S is where I will land. It'll be blk/blk or blk/tan and a 6sp manual. Options.....xenon, Bose and heated seats. Anything extra will be a bonus. I am hoping a 40K mile or less car can be had for $17000-18,500.
Good luck in the search.
John
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