If you special order it (or maybe a dealer has one lying around) the Dakota is available with AWD. I have a 4.7L Quad-Cab 4x4 (without the AWD transfer case) with the towing package (including 3.91 gears). It is a very capable and comfortable vehicle towing ~6K, and it makes a nice daily driver. The only downside is that the fuel economy on the "modern" 4.7L engine is no better, IMHO, than it was on the "ancient" 5.2L (I get 14/17 and ~13 towing). The upside is that it seems to have about the same performance and a lot higher redline.

In any event - one of the most critical things is that you have adequate trailer brakes. That means having a GOOD controller and adequate wiring to handle the current. Additionally, plenty of tongue weight (~15% of total trailer weight) and a good equalizer / sway control hitch will help keep you out of trouble. I've seen the consequences of not observing those rules, and they are not pretty.