On the dodges, don't be scared of them because of age, I'd go into the early 90's readily. My dad bought a '92 with 300,000 miles that runs like a dream, the first generation trucks are better trucks all around than the 2nd generation, pretty trouble free transmissions, best fuel mileage, and will take the most sh!t-kicking of any truck out there, they have leaf spring front suspension, which may not ride the smoothest, but is the least maintenance by far, kingpins rather than ball joints that always die, standard wheel bearing that you can repack as opposed to these unitized things that you just have to replace now, and they're MADE OF METAL.
Everyone I know would rather have the 12V engine (pre-98.5), some of the early 24 valve engines had bad block castings that would crack, and the injector pumps are no where near as reliable. I heard good things about the mileage you get out of the "common rail" trucks, which was about 2003 or something, but don't know much more about them than that. 6 speed trannies are very nice to have, but if you don't abuse them, the 5 speeds with the nut fixed are pretty decent... What can I say, I'm making over double the stock power and torque, and it is the weak link.