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I have a 2006 Cayenne TT. I bought it CPO about 6 years ago. Despite being 13 years old, it still hauls the mail.
RKD, OneWhippedPuppy, and David summed up the issues of different years/models.
For reference:
955: 2003 - 2006 models
- oldest, cheapest, and least attractive exterior styling
- identical interior to the later 957s
- very capable vehicle with H/L transfer case and 7500lbs towing capacity
957: 2008 - 2010 models
- essentially the same car as the 955, with a facelift
- handsome styling, better (bigger) brakes
- some risk of bore scoring on the 2008/2009 V8s which is a big bummer
- direct fuel injection gets better fuel mileage
958: 2011 - 2018 models
- newer, more jelly bean body style
- weighs 500lbs less than 955/7s
- better fuel economy, faster performance and better handling
- more modern interior
- lacks H/L transfer case (but honestly, no one ever used it)
- Additional performance options like active suspension and torque vectoring
- Diesel engine option
In my opinion, the Turbo is almost always your best used value/choice, unless you're really focused on lowest purchase cost and/or best fuel mileage. The turbos have enormous power and are usually spec'd with (most) all the options including air suspension, which is also a must. The Cayenne air suspension is one of the best - - sporty and comfortable, even without active suspension.
My personal opinion is that they all require regular and proactive maintenance - - in my experience, that works out to about 15-25 cents per mile (excluding fuel) for DIY maintenance depending on highway /city and driving style. As mentioned above, they eat tires, brakes, and gasoline. I get about 10mpg, and ~15k miles on a set of tires. But the smiles are worth it.
I would never recommend one to someone that does not do their own wrenching. Dealer costs for maintenance on the Cayenne would be a total nightmare - - easily 3x my estimate above. Cheap (<$200) Porsche-specific scan tools can diagnose/reset most everything on the car, and the DIY community/forum support (RennList) is very good.
Each model has some bug-a-boo repair that costs several thousand to fix, but it's usually a once and done (or a once every 100k miles) issue. The only heartbreaker issue is bore scored V8s in the 2006-2009 manufacturing window - - Google that before you buy one. A Cayenne with a blown engine is a most likely a part out car.
The Turbo S and the GTS models carry a collectible premium. Not worth it in my opinion as the "regular" turbo is not much different than the "Turbo S" levels of performance and clearly exceeds the GTS (although the GTS does often have slightly better styling and did come with a 6 speed manual option which is coveted by some).
Good luck!
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