What is the weight of the boat package? How about tongue weight?
A neighbor has a 2000 Limited 2WD and pulls a 19ft Carolina Skiff to the boat landing seven miles away. I think the boat, trailer, and works comes in around 2300 lbs. With close to a 8% grade, it pulls it up the ramp just fine. Having just put new Cooper tires on, he told me that has helped with wet traction, especially at the ramp.
If you don't have new tires, make sure the pressure is low in the rear for better traction, especially if the ramp is algae infested. And add a tranny cooler.
If doubt still lingers, buy a 99-2000 Limited with 4WD or 2001-02 with 4WD.