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It's impossible to tell what will become a classic. More than likely older Boxsters will be worthless in a few years. To even be worth buying as a 'collectors item' you would have to keep it in mint condition for a few decades.
I would much rather enjoy my Boxster now, and not worry about what the car will be worth in the future. I have no intention of ever selling my Boxster and it will probably be worth far more to me when I'm older than to a car collector.
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1999 Ocean Blue Metallic Boxster - blueboxster.com
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