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Boxster (S or not) or 996 cab.
He's not a car guy. He's not a DIY guy. He's not going to want to deal with the maintenance or idiosyncracies of any air-cooled-vintage 911. Those are more likely going to sour him on the Porsche experience than bring him into the fold. Most people (particularly the non-car people) want Camry-level conveniences and reliability in whatever vehicle they purchase, Porsche or not. 'Course, you know your friend better than we.
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1987 Venetian Blue (looks like grey) 930 Coupe
1990 Black 964 C2 Targa
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