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I had a 2005 4WD ext-cab Chevy Colorado and was able to get ~31 mpg (the records are on this site). It had the 3.5L (5-cyl) engine and 5-speed manual trans. That was with tonneau cover, tires at 40 psi, and a lot of hypermiling. Based on that, I'm guessing a 2WD reg-cab Colorado (or GMC Canyon) with 4-cyl (2.8L) could come very close to 40 mpg. The S-10 should be similar.
Rather than drop an underpowered engine in, probably an easier solution would be to just swap out the rear gears to something very tall and/or a taller-geared transmission.
Ultimately, I agree with Frank Lee above, though. The best solution is to get a good 4-cyl high mpg car and just tow a small utility trailer when needed.
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Daily driver:
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