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The 2002 996 Carrera 4 Convertible. I've rebuilt the engine myself (drove 6K+ miles since), added solid trans mount and 19 inch lobsters.
The 2006 Cayenne Turbo S. Our 5th family member for the last 7+ years by now / 60k+ miles. Went through all common tech issues with it so far. We take the "U" in SUV by the word - be it by transporting all sorts of recreational stuff on the hitch rack , pulling trailer to riding dunes. It is a massive pig of a car, but so far this is the one with the best acceleration, and a joy to drive every time.