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I bought a 2004 Boxster S. I will admit that they look like baby 911's but the fun factor per dollar is inverse of the 87 911.
Much more fun to drive than my 87 911.
I love the Caymans.
If I only had 1 Porsche, even though IMS failure rates are very low, it is unacceptable to me to have a car that this can happen with. So, the gen 1 Caymans are my favorite car to drive. The caymans and the boosters still have that more raw feel of the old 911's.
The newer 911's are GT cars.
For me, I would buy a 2009 or newer Cayman S.
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