Andrew - I may not have given the new Durango a fair look and thanks for the updated information. But, the experience we had with the Cherokee tainted me. Not sure how to describe it but flex/float is what it felt like - and that was towing a 3000 lb. trailer pre Airstream days. We changed out the tires and shocks and that helped a little but not enough.
I had no complaints with the 98 Durango. The tires were changed out and Monroe SensaTracs added. It towed great.
ZZ - my first choice was the 11 Dodge Crew Cab with the 5.7 Hemi. But around here they are in demand and the dealers have very few on the lot. I just couldn't get them to work with me on pricing and we didn't like the feel of the cab. So we ended up with the first Chevy we ever owned.
It's a 2011 1500
Silverado Crew Cab LT All Star Edition. That gave us the HD suspension/trailer package the locking rear differential and manual override 6 speed auto. transmission. We dropped down to a 3.42 axle and a 5.3L vortec V8. It has 315 HP versus the 98 Durango at 245. The torque is the same as the old Durango at 335 ft/lb. We picked an additional 28 inches of wheel base.
I've not towed with it yet but so far I like the way it handles and responds - and it's one comfortable truck. We may end up changing the shocks to SensaTracs after we tow with it once.
But, that's not comparing it to the OP's question about the 11 Durango - which again - I may not have given a fair shake. Brian's right on the multiple opinons. Towing comfort is such a personal thing - it's hard to give anyone advice on a vehicle. You really have to drive the it and see how it feels under your keister.....