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CommonApp is 840 words so far...kind of nervous bout that.
Yale supplement is 812, so I know I have to shorten that a lot. The essay will definitely be worse when it's shorter, though.
Yes, try to keep both under 500. They WILL read longer essays, but it's better to follow their recommended instructions. And yes, it only says it for the supplement, but you want to keep your common app around there too.