I've got a 2000 4.7 L Dakota Quadcab with the trailer package.
Pulled a 4200-ish lb 20' Four Winns like a champ (better than the 99 5.7L Tahoe we had). Would run at 70 without breaking a sweat.
I thought long and hard about getting a flatbed for the Jeep and ATVs. I even hooked one up (16' beavertail). I solicited comments from those that had done it and got some great feedback (see below).
I finally decided that it just wasn't enough truck. It's rated for 6000-ish pounds, and I don't think power would be the issue. I'm concerned the trailer weight would push the Dakota around (2000 lb trailer + 4000 lb-ish TJ). Around MI it would probably be fine, but I would want to tow it to KY, PA, Canada, and out west, and that's where I think the Dakota would be over-matched. The last thing I need is a broken tow vehicle.
If I had an aluminum trailer (1100-ish lbs) I might go for it, but that adds $3K to the trailer cost.
I think I'll look into a flat-tow setup for the TJ - the Dakota should handle that fine.
This is the Pub. Leave common sense at the door.