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I traded my Dodge 2500 diesel for the 04 Lariat Screw. My first loaded truck. Now there are times for work that I am not happy because it is too nice to use, or too short in the bed. I am actually considering going back to a single cab truck, stripped work model. Will make it more difficult for the family, but much more versatile at work.
The GMC's are much cheaper than the Ford or Dodge, for the work truck model that is. I am weighing my options.
I think you are going to take a bath on the trade in value now. A Screw is light years different from a dodge diesel. I would get over the "too nice to use" stigma. Its a truck, and you shouldnt worry about it. It is made to take the abuse, and keep on motoring. As for too short in the bed...well I assume you had the bed length in mind when you purchased it.
We have a '05 F550 flat deck at work. It pulls a trailer with out manlift on it. About 10000 bls for the tow. The truck runs pretty good, kinda a pig on the diesel.
You can always go for a XL supercab. You can get either the 6.5 or 8ft bed, back seat and an interior you can hose out if you want. From your post, it would be the perfect truck.
Ya that sounds like the way to go. buy the work trunk then add all the goodies for inside as options. I went with the XLT because I wanted the power options.
If its too nice get some neoprene seat covers that you can wash. Some plastic catch all floor mats. As for the bed get a bed extender, it works miracles.