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To answer your question, I do not think you are crazy to upgrade to a 911.
I just wouldn't buy the 996 version because the scenery doesn't change from inside the car. The 997's interior, like the 987 is much nicer.
But to each his own. You may love the quality and looks of your boxster's interior.
When things turn around for me financially and I can successfully wear the wife down enough to consider it, I will probably purchase a CPO 997 C4S and sell my boxster for whatever pittance I can get out of it.
The 987 cayman's are nice, but they still have the IMS and D chunk prone M96 motors in them.
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