oh geez^^

 

some models need an oil pump, but thats really it,
i've got the 2007 flat towing guide sitting around, its a good couple hundred pages of flat towing tipos/tricks, and a complete list of the new vehicles and towing specs,
my parents have been flat twing behind the motorhome since i can remember

 

As far as the weight is concerned, you should be fine. A stock Grand Cherokee with the 5.2 V8 weighs in at just over 4100lbs, if memory serves me right. That is well within the capabilities of the Dakotas. The problem you may encounter, as pointed out by "ta8sa", is with breaking. I use my 01 QC 4x4 auto with the 4.7 to tow a 4300lb boat without problems, I just can't be in a hurry.... (I do have a tandem axle trailer with disc breaks on all 4 wheels, surge activated).
No matter what everybody's experience here is,be carefull not to exceed the allowable capacity based on your trucks options. Doing so can get you into hot water should an incident happen.

 

I've towed a good 10k pounds for about 50kms. I took my old 74 F250 to scrap, it was full of scrap too. it about 8k and the trailer is about 2k. and it handled it pretty good. you just have to take your time

 

the biggest issue i should have pointed out, but i didnt think about it
Rolling mass,
a stock jeep can get hauled pretty easy, but with 33's your earth drag, or rolling mass is much greater,
as it is harder for the jeep to turn the tires, it's also harder for the dak to get them moving too.
if you put stock tires on, you'd be fine