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Well I could make a guess but if it's wrong won't the IRS kick it out as a mismatch 1099-DIV amount?

Nope, the numbers on the extension form are a guess. Btw, guess high, and then you can get a refund later. If you guess low, you owe penalties for paying late on the remainder.

An extension won't help if a duplicate 1099-DIV is sent and again "misplaced".

Well, it'll get you 6 months more to stop having it be misplaced. Can you ask the nearby friends to check the mail ever day and segregate (or even hold onto) anything that loks tax-related.

I agree its not ideal, but I think a request for an extension with an payment of what you expect she owes is absolutely the way to go. Then how to get the information to stop being misplaced is up to you, her, and those who assist her daily.
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