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After a bit of searching I Just purchased an 06 cayenne turbo with 100k miles. I read through all the good and bad. It was between the I bought and 08 turbo and an 06 turbo S. This one and the S had the coolant pipes fixed. I really liked the 08, but it smelled like coolant when I popped the hood, and he couldn't produce the service records he claimed he had, so I passed. I picked the nicer of the two between the turbo and turbo s. Luckily I have modded a lot of different cars so I think I am capable of fixing anything that goes wrong. The thing I love about performance cars is that their owners love to do detailed write ups, and I find the Cayenne crowed is no different. I also picked the 4.5 because if it blows a motor, the junkyard sells them for $4k compared to the $10k for the 08 and up. The only downside for the one I bought is that the factory wheels are trashed from paint coming off. I am going to use those for winter wheels and buy some 20" aftermarket or maybe GTS wheels in 20" (I haven't figured out if the GTS will be correct on the offset yet). This will be my first experience owning a Porsche, I hope it is a good one as I would like to own a 911 or a Boxster gts one day.
I'll be selling the 21" wheels from my 09 TTS in about a month. If you're interested I can add you to the list of those whose expressed interest. Will come with the 295/35 Pirelli tires currently on them (fronts are good, rears will need to be replaced) and TPMS sensors for $2,500
20s, though they ride well, look a little too small on the higher end Cayennes.
I went through the same thought process and ended up in an '04 Turbo with 105k miles. Maintenance history/records trumps everything else. I contacted 2 Porsche dealerships, and an independent shop to confirm that all of the usual suspects had been addressed except the starter, fuel pumps and cardan shaft bearing. A week into my ownership, the fuel pumps died, with a FULL tank of gas.... because Murphy's law. Took my time and knocked it out on a Saturday morning.
If you can get your hands on a CarFax report, reach out to the dealerships mentioned for maintenance records. The ones I dealt with were great. One wouldn't share any owner info but read it all out to me on the phone, the other dealer - local to me - printed everything out and handed me a stack of records with the prior owners contact info. Go figure.