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I think in a few years when the 25th anniversary of the first Boxster rolls around (and likely when Porsche introduces the next gen update of the 718) you'll start to see some interest in older 986s from a collectors perspective. But just like with any 'collector' car, only very early or limited edition models might see some appreciation.
1997 Boxsters with less than 40,000 miles (in original, VG+ condition). Bonus for Silver w/red interior and a hardtop.
2004 550 SE's
And possibly some first year S models from 2000.
And just like with 911's, it will be low-mileage cars with full maintenance history that will be of interest, as they become few and far between over the years.
Do a nationwide Craigslist/Autotrader/etc search for a 97 Boxster with less than 50k miles. You won't find many.
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