I'm going with the Jeep as well. I am biased, having my sixth Jeep Wrangler (2005 Unlimited) parked out in the driveway, but there's nothing quite like a Jeep. Doors off, top-down in the summer, 4x4 engaged with the hard-top on in the winter... it's the best of both worlds. The Jeep community is friendly (as mentioned previously) and the vehicles are agriculturally basic so seldom break down. When they do, parts are dirt cheap and there's a world of enthusiasts out there to help you out if you're a DIYer, and if not, any corner garage in the continent can get you back going.
How easy would it be to get your Cayenne S fixed in Armpit, Arkansas when the plastic coolant hoses inevitably crack and fill your engine valley with anti-freeze?
Fellow Jeep owners, this is for you!