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Matt --
Agree that the ownership experience is very different between an SC and a 996 (obviously), but the economics should be similar (barring outliers and catastrophies).
From the OP -- the hard part is calculating the residual value of a Porsche after 20 years, or 40 years.
In the short term -- new p-car stuff seems to hold its value pretty well. I know of a 2011 turbo S that sold recently for 88% of its MSRP. It wouldn't surprise me to find out it sold originally for that same amount.
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