If you are going to move any weight (10K+), stay away from the PS with automatics. I've had 95, 99, and 01 duallys that I tried to take care of (fluid/filter changes every 25k miles) and still had to put multiple trannys in each of them while I owned them. Otherwise, they were all great trucks.

Is this going to double as daily driver? How often are you going to be pulling a trailer? How much weight are you pulling? How far are you pulling it? Those are the questions that you need to ask before you pull the trigger on a diesel truck.

You need to weigh the maintenance and inconveniences of a big diesel vs a gas burner to see if it suits your needs. The maintenance costs of a diesel may make it worthwhile for you to start out with a gas truck with a lighter trailer, then move to a bigger rig when you get more involved.

FWIW, I moved to an 05 F150 SCrew when I no longer needed the bigger trucks. I occasionally pull my Mustang on an open trailer, and I have a 8k lb 32' travel trailer that I try to pull about once per month. This truck handles both with ease, though I haven't taken the travel trailer through the mountains yet.