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The 98 boxster is long out of warranty and I do the work on it. The 2010 Cayman S is standard warranty, it is ordered and not here yet. But I am not a fan of extended warranties as a rule.
I have an 03 Range Rover HSE and I looked at an aftermarket warranty on it but after getting into the nitty gritty of it, there were too many exemptions to make it worth while to me. Like it only covered failures for oiled parts. For example a blown head gasket is not covered because it is not an oiled part.
It sounds like you like to get your hands dirty as I do. I am meticulous about my vehicles and most average auto repair shops quality of work is far below my minimum standard, so I do it myself.
I have a friend with a very sucessful Lamborghini, Ferrari, Porsche shop. He used to be a factory mechanic at Lamborghini, he is Italian. Not a "pimp my ride" kind of place but a real repair shop, he actually worked on a Veyron recently. I have learned so much hanging around his place. What I learned is that his expertise is in his head because he uses the same basic tools that I do. Nothing special, he just knows what he is doing and does it well.
I will have the Cayman S serviced at the dealership during the warranty period but after that it is mine!
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