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The key was not labeled "this is a key to Erebor" and Sauron probably didn't bother to look at the map, since it showed the Lonely Mountain, which he knew. Maybe in the lust for the Ring he didn't even look at it. And if Sauron wanted to ally with Smaug, he'd probably send some of his classic Horsemen In The Night through the front gate. It does look suspicious if you sneak through the back entrance to a person (or Dragon) you want to make a fair deal with.
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"Should the story say 'he ate bread,' the dramatic producer can only show 'a piece of bread' according to his taste or fancy, but the hearer of the story will think of bread in general and picture it in some form of his own." -On Fairy-Stories
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