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It's an emotional thing. If the shape, sounds, and "feel" of an aircooled tug at his heartstrings, then buy the newest aircooled he can find. The 993s are stupid expensive, but you may find one.
But a 996 is the best value for a get-in-and-go 911 shape Cabrio. Cold A/C, stable temps, not as many leaks and issues.... the most modern feeling Cab for $25K.
A Boxster just isn't a 911, but may scratch his Porsche itch. He'll know right away.
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I love you guys outside this forum 
-Eric
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