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The biggest functional difference between the KL Cherokee and WK2 Grand Cherokee is the fact that only the Cherokee has a proper mechanical diff lock (Trailhawk version only). This alone will make the KL much more capable off road. I don't know if that's a significant criteria for you, but it's worth considering if you plan to go off-road.
The Grand Cherokee can be lifted for more ground clearance (if you avoid the mixed-reviews air suspension) while the Cherokee cannot. Another potential factor to consider, depending on your intended uses of the vehicles.