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If you can get into the mid to high $30's, you can get a certified 996 car, which means at least 2 years of warranty coverage for drivetrain....
Loved my 87, which I just sold this spring with 38,000 miles on it (for $22k BTW), but the newer cars off lease are steals right now....
Don't think I like one better than the other. So much is the same, and yet so much is different with them.
Porsche made the air-cooled 911 about perfect through the years, and the 996 was all-new. Porsche is small too, so I'd stay away from any ofthe earliest years of Boxster or 996. Interior improved quite a bit in 2002 or so also....just my $0.02.
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