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If it was me, I would buy the 59. You could always swap the engine out after a while to a more common SBC at minimal cost. But havig that rare V8 will only up the value of that truck as the years go on. As much as I love the 67-72 style, the 55-59 is still the nicest Chevy body style produced.
Does the 59 still have the solid front axle or has it been upgraded to an IFS system? If it's solid axle, you wouldn't really want it as a daily driver. It would be like driving a lumber wagon
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