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I haven't explored the code yet, but this article states that categories are assigned to permalinks based on the category id. That makes sense to me, considering other WordPress code that I've reviewed. So, the order in which you add the categories would determine which one is selected. Although I can't recommend a specific permalink plugin, it sounds like you need the fine control that a plugin could provide.
Toggle Commented Feb 9, 2012 on Wrangling Wordpress–need help at
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Feb 9, 2012