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I don't own either a 986, 987 or a 981 yet. But I have often thought about the same thing . The way I ended up rationalizing is that the fun of owning a 981 is not 60,000 dollars (in your example) for fun to drive. But then again you have to realize the residual values of your 2 car are going to be at least 40 to 50 K apart for the first couple years at least.
Say in a year the new car would have depreciated to 65K and the older one to 17K - the difference is 48K. So the question in my opinion comes down to whether buying a car with exactly the options you want, the color and the latest gadgets and technology worth 12K? Also the cost of maintenance in the first 4 years on your new car would be minimal compared to the same for the older car.
In my case I choose the older car only because I do not have 80K to put down. :>)
Cheers,
AJR
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