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It's all about the right tool for the right job. My wife's RX (essentially an early production Highlander) is an absolute bore to drive. Terrible steering, feel, even sound. That said, she doesn't get satisfaction from any of those less tangible assets and it's a great car for her.
On the opposite side of the spectrum is the Audi Allroad I would have preferred. Do the transmissions tend to have issues? Yes. Air suspension leak? Yes. Need new control arms/bushings every 100k? Yes. The RX needs none of these things, but shifts like a vague sort of rubber band system in the transmission I would rather throw in the trash than fix. Doesn't have any steering feel at all, so I would never know if the bushings were bad. And it obviously doesn't have air suspension to leak.
There are Honda buyers, Porsche buyers, and everything in between. The people who shy away from Cayennes are those who A.) buy them out of warranty, and B.) didn't know what to expect. For the vast majority of people, a Highlander is a better option. For the small minority who know what's what, they can get cheap under-maintained Cayennes all day long.
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