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So I would like to set two separate feature images for each post/page. One would be a rectangle for use in a slider and another would be a square for use on archive pages, search pages, category pages.

WordPress can do this, but it either resizes the initial image to the nearest resolution or crops it. I would rather create it myself and upload it.

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This plugin is what you're searching for...

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This is very helpful. No idea how I missed this while searching! –  nothingtosee Apr 25 '12 at 9:47
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