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Adding the word 'Grand' to the Cherokee turns it into a real Range Rover rival. This is a big 4x4 as only the Americans know how to make them. It's massive inside, generously equipped in high-spec versions and a highly comfortable place to spend some time.
The original Grand Cherokee was replaced by the second generation model in 1999, offering more rounded styling. It also got a more modern range of engines, including a new 3.1-litre, five-cylinder turbodiesel, a six-cylinder four-litre petrol and a big 4.7-litre V8. The diesel was, in turn, replaced by a 2.7-litre CRD engine in 2001. All have very smooth automatic transmissions.
Of the engines, the preferred choice is the diesel, as the petrol units are very thirsty on fuel. The engines are reliable if serviced properly, but the auto transmission can develop leaks.
It has great off-road ability, so check carefully for signs of abuse on rough terrain. The chassis or underbody could be damaged or there may be extra suspension and steering wear. Check that the steering tracks straight, without pulling to either side, and is smooth from lock to lock.
Build quality is better than many Jeeps - it is built in Chrysler's Austrian plant - but wear and tear on the interior is still a problem. Also check all the electrics, as components tend to develop faults.
http://www.topgear.com/drives/B9/A2/used/