[onewhippedpuppy]

Unless your hypothetical friend is a DIY enthusiast type, recommending an older used Cayenne means they're not going to talk to you within a year. They aren't known for being particularly reliable, they're very complicated, and much of the service/repair work will require a dealership or specialist independent shop. Remember, most of the population DOESN'T think wrenching on their car is fun. I have the same problem when asked to recommend cars, what I would get doesn't mean it's the best for my non-enthusiast family and friends.

So for me it's the Jeep, all day long. It's simple and reliable, the new V6 is a HUGE improvement, you can take it anywhere without worry but it won't beat you up daily, the top comes off (try that with the Cayenne), and they hold their value insanely well. Plus it will have a full warranty, Jeep dealerships are everywhere, and any shop will work on it. Get the new color matched hard top Rubicon, they look sweet. Given a few years worth of depreciation I'll be shopping for a Rubicon Unlimited with a 6-speed, a friend of mine has a 2011 model and I love it.