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The weather stripping at the corner of the door is crushed.  Replacing it would be a good first step.  I've suspected that Jeep builds this way to add a little feel of roughing it even in the city.  The hard top gutter ends right about where your weather stripping is crushed and drips when you open the door, which just plain poor design since it could run forward a little more and eliminate the drip.  Of course a lot car makers don't even bother with a gutter any more..