Thinking about a Cayenne
#16
Drifting
I don't know about that. I've done at least one valve body on an '06. I would personally lean towards an '04-'05 with good records, unless you're looking at a Turbo S.
#18
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#20
Track Day
B. I had a 2008 Touareg V10 tdi... it was pretty awesome in many ways and the torque was lovely. 553 lb-ft. It was finished nice enough.
C1. fuel prices????? when considering suv's mpg. v8 vs tdi, the tdi versions provide more than enough higher economy to offset the VERY small difference in fuel pricing. Normally diesel is only 2.5-5% higher $ while the tdi engine is easily 30% higher mpg. This is simple math. I'm very tired of hearing people say "but diesel costs more". This it not an emotional equation, it is very basic math. For example, even babying a v8 touareg/cayenne maybe you can get 20mpg, while less babying the throttle will yield 25mpg+ (25% higher). Fuel differences would have to be $4/g premium vs $5/g diesel to equate that ratio.... and they never have been in all my years of traveling the country. More common is a ratio of $4/$4.25. Even $4/$4.40 is still only 10% leaving you with a diesel advantage of 15-20% in actual driving.
C2. Then factor in the range returned by diesel especially when discussing long trips. This is where the Touareg 2 v6 tdi or Touareg 3 v6 tdi shine returning upper 20's to 30 mpg on a 25 gallon tank. All while being rated for 7000+ lbs towing.
The best picks in my opinion are:
T1 V10 tdi, because they are cheap
T2 V10 tdi, not as old, still good value, $30k ish for 2007 (2008 still commands a premium and are hard to find) 2008 is last year with 4 zone ac and some other nice features
T2 v6 tdi, 2009-2010, 2009 is still $30k or less, best fuel economy and still retained air suspension. 2009+ has better nav/touch screen. Newer than 09 is sort of pricey for a used VW compared to what you can get in a Cayenne that is older but much higher spec.
For comparison, the Audi Q7 is rated higher for towing and was available with air suspension and higher spec overall than VW's but less fun to drive, much less, than either an X5d or Cayenne.
Mercedes GL will tow as well or better than all of the above simply due to the long wheel base, has huge interior (the Cayenne/Touareg are rather small inside for my gear). GL has air for load leveling, very good fuel economy for it's size, big fuel tank. Last year with full size standard spare was 2007, maybe 2008. CDI diesels didn't have the ad-blue stuff which newer ones do.