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Since they are Corvette people, a newer version seems like the better, safer choice over the MK I 996. I am "911 people" and I prefer a nice C5/C6 over a 996.
If they have an itch to try a 996, suggest the MK II version, 2002-4. They come with a hp/torque bump (320 hp vs. 300), glove box (not in 99-01) and the cab comes with a glass rear window. 99-01 cabs had plastic rear window. I agree with the points about pricing and buying from someone who can show the service history on the car.
Having said that, consider a well sorted 993 if they really want to move into Porsche ownership. That's what I'd be shopping for if I didn't already own one.
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