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#1
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You should have no issue whatsoever towing a boat with any Jeep. Also, you should have no problem pushing a boat with someone else, even on a slight hill. Just dont let it get a rolling start.
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#2
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that combo is around 2300lbs w motor and trailer, maybe a little more, a grand cherokee can tow 5-6k pounds, my buddy tows a porsche and trailer w one long distance around 5k pds. Just be careful and look the boat over well, a 1990 is gonna have alot of rigging done to it so be sure you know what your buying. the older suzuki 2 strokes are gas and oil guzzlers but skeeter always made a nice hull, Im sure its a hell of alot better than the tinny your fishing out of now
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#3
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If you can push the trailer up your street then it should be able to back it up with your jeep, depending on where you live I'd show you how.
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