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I would believe it's through trial and error. But usually, the quickest way to do it in my opinion is to see what is different. For example, if you're drawing a lewis structure for something bonded to 4 oxygens, with 1 single bond and 3 double bonds to oxygen), and so the resonance structures would be changing the oxygen that has the single bond. You know it can have 4 possible positions, and so you would have 4 resonant structures (one for each oxygen).
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