Re: 2001 jeep cherokee sport w/ 20' 2005 trophy walk is this ok?
Three words:
Brakes Brakes Brakes!
I also have a Cherokee and I tow about 3500 with it. I have on occasion towed 6k with it for an emergency. The I6 and the AW4 (if you have the auto trans) is a great powerful combo with lots of low end. your jeep has a tranny cooler built into the lower portion of the radiator, its not the best ever, but it works, I would upgrade if towing lots of hills. The brakes on the Cherokee even in perfect condition, are marginal at best, you will need lots of brakes on your trailer. I also installed rear air bags. best 200$ I have ever spent on my jeep. you can easily adjust your ride height (keeping your weight more balanced) , and keep the rear from riding on your bump stops if heavy loaded.
what does your combo weigh? you can easily find the specs of your boat weight, find your total fuel weight, and trailers are in the neighborhood of 500 lbs or so. Keep in mind if you are rated for 5k, I couldn't tow much more than about 4000 to about 4500 very very max. it is much better to have that safety factor. if you get into an accident with an trailer that is more than your car is rated for, you will instantly be at fault. ( here in california anyway!)
Edit: you are lucky also your jeep came with the stronger 8.25 Chrysler axle, not the wimpy dana 35!