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Q: Does putting a series of covers together offer more or less challenges?

A: I think a series of covers is much easier. Turd Theory (one of The Twenty Irrefutable Theories of Cover Design, written by myself and Jon Gray) works on the idea that in a scary world of disorder and chaos people are programmed to seek out repetition and order. So even the worst cover in the world, repeated 20 times in different colours of the rainbow will get you an award or two.