Goals are crucial. You'll be amazed at how much harder you'll work when you have one.
One of my trucks is a 1987 Chevrolet R10 (Half ton). It only has the 305, but it's plenty of truck for me.
Chevrolet/GMC switched from carbed engines to EFI for the 1987 model, so I'd probably go with an 87 or newer (Unless you're comfortable working on a carburetor). The 1987's hold their value well- they're the last year of the body style, and the only year of that styling with fuel injection.
I used to have a 1989 3/4 ton. They're great trucks, too.
I'd look for a half ton with a 305 like I have. The fuel mileage is a little better than the 350, and it's still plenty of truck for most things. I've hauled plenty with it (I have 1300# on it now). Even with the trailer on (1000# in bed, towing another 3500#), I was able to do 55-60 MPH easily. The 305 isn't as powerful as the 350, but it sure beats my Ford 300. In my mind, Chevrolet trucks are far and away superior.
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