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Currently owning several Boxsters and a '90 944S2 Cab, I'd say keep the 944 if it's in top notch condition.
I've had my 944 for 20 years. I can find a ton of 986 cars in outstanding condition without having to look hard, and they'll be available for a long time. A nice condition 944 not so easy...
Just my 2 cents worth...
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I think I have a Porsche problem...
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