I got my Sierra, 4x4, crew cab, etc. for under 30K a little over a year ago, when GM had employee pricing for all. It was a better deal than used at the time.
I need to carry 5 adults, plus either 3 motorcycles or 6 mountain bikes or some combination in between. That left my choices with GM, Ford or Chrysler products. I don't think Toyota, etc. builds anything like my 2500HD.
Your towing needs are very likely much different than mine.
I like having 4x4 because I sometimes use the truck to go skiing in the winter. And, my favorite campsite requires that I cross a dry creek bed, dragging the TM rear hitch receiver on the ground. 4wd and low range is very helpful for that situation.
If you never get off of paved surfaces and never encounter ice and snow then 4wd is not necessary. You might consider a limited slip differential 2wd instead. I would not settle for less than limited slip 2wd.
Spend some time figuring out what your requirements are. If you are not sure, this is a good place to be thinking out loud.
Regarding drafting behind a big rig...
there was an episode on the Myth Busters not too long ago where they documented that you can in fact improve fuel economy by drafting behind a big rig, but also that you need not tailgate. Just follow the rig at the normal safe distance and it will help.
I ran a drafting test recently, using the mpg display in my Sierra and I gained about 1 mpg drafting versus not drafting. This was not using high precision test equipment.
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