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I think Techweenie's advice sounds the best. Granted I've only owned one 911. But IME you're constantly wrenching (admittedly on little things) on a 20+ year-old car. And when you throw in bang-for-the-buck criteria, those air-cooled cars aren't so cheap any more.
You can have your pick of 996's for $15-20K, and as long as you don't get one of those uncommon RMS/IMS fatalities during your tenure of ownership, the car's probably going to be more reliable than most air-cooled cars.
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1987 Venetian Blue (looks like grey) 930 Coupe
1990 Black 964 C2 Targa
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