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I am considering 2005-2010 Cayennes and I'm wondering what to look for. I found an '04 Turbo with about 145k on the clock that I'm pretty interested in and there are several S versions local to me. It seems these are well liked and reasonably reliable from the research I've done. Is that true, or do I run like Hell... I currently own an '06 LR3 which I off road fairly heavily. I am not afraid of a higher than normal rate of "routine maintenance" to keep things tip-top, but I don't want major systems that take a crap repeatedly. There are plenty of these in the ski town where my wife and I work and live next to, so I can be very picky and find one that's well maintained. I just would like insight on what to look for.
 

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Do yourself a favor and get the 2nd generation, 2010 or newer. You will be much happier.
I can't agree more here. No brainer to get a second gen, Model years: 2011–2018. Unless you want a car to strip down and off road or something.

I have a 2011 S as my daily driver with 144K miles on it, and still love it as much as the day I got it. Turbos are not worth it in my opinion, unless you are a car guy/wrencher and really know how to do it all yourself, bc these are more expensive to maintain, considering parts and repair process. My V8 S is plenty fast and powerful for towing.

The 2nd gens are much better on gas mileage, lighter, and have all the modern elements you would be looking for in a new car. Plus, the interior is night and day. My interior still looks like a current Panamera, that's how little they have changed. Getting into a first gen cayenne is like sitting in a time machine, it just looks and feels old.

Once I added the JoyeAuto Wireless Apple CarPlay to my Cayenne, I have zero interest in a new car, as it looks and drives great, with all the modern features. I can't endorse this upgrade enough to Cayenne owners BTW!
 
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