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I am on my second Cayenne. My first was an 05 V6 which I had for a year and a half. It was a great car and did have the driveshaft support bearing issue. It was a very easy DIY to replace the shaft. I had no other issues with it, major or minor, but the interior felt a little cheap. The vinyl dash never appealed and I replaced the plastic trim with wood which made a world of difference. It definitely felt underpowered, especially when overtaking or merging on the highway. I traded it in on an 06 S with full leather and light olive wood trim. The difference in power is remarkable between the V6 and the V8.
As noted in the other posts, the driveshaft support bearing, the coolant pipes and the ignition coils are the weak points in the car. I replaced the coolant pipes in about six hours using the pelican how to document and supplemented with rennlist posts. It was relatively easy but you'll need some triplesquare bits and e-torx sockets to remove the involved fasteners. The aluminum coolant pipe upgrade kit is made by Porsche and is around $600. You'll also need two gallons of Porsche coolant and I highly recommend an airlift coolant fill tool to check for vacuum after replacing the pipes and to fill the engine without air pockets.
I have not had the driveshaft support bearing fail *yet*, but it eventually will. Rather than replace the whole driveshaft this time, I will use Vertex's upgraded support bearing which can be installed easily and is considered a permanent fix. Replacing the shaft only means the new bearing will eventually fail, necessitating another replacement in time.
The coils are a breeze to replace. I did all eight in about two hours, if working VERY leisurely or in about an hour if you work straight through.
Another not-uncommon-but-not-frequent issue involves the fuel pumps. They are a known failure item although not an overly common one. There are two pumps, both located in the fuel tank and are a bit of a pain to replace.
As far as options to look for, I would really recommend the full leather package. The interior is so much better with it than without. Having had both, I would never get another one without it.
The base CDR-23 cd player is abysmal and is very expensive to replace with an aftermarket head unit due to the Bose fiber optic based speaker and amp system. If you can live with the limitations of PCM2.1, I would look for a Cayenne with that instead. If you are intending to replace the head unit, budget around $2k for a quality Pioneer or Alpine unit with the associated harnesses to integrate with the Bose system. There is a Chinese knock off unit for around $700 that purportedly integrates with the Bose system but rennlist has a couple of threads discussing its limitations.
As another poster mentioned, with proper snow tires, the thing really is unstoppable in winter. With good summer tires, the thing handles like no other SUV and can shame more than a few sports cars.
Air suspension is a nice to have item and I've driven several Cayenne's with it. Both of mine have standard coil springs and the ride is quite nice. Air suspension really helps if you use wheels larger than 20" as it takes out some of the ride harshness that the reduction in tire sidewall introduces.
If you want to tow anything, I highly recommend the S or, even better, the turbo. Towing with a V6 was a miserable experience and one of the biggest reasons I traded it for the S.
If the one you're looking at has a good history and is in good mechanical shape, go for it. You won't be disappointed.
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