[HAL9000]

I THINK I've got it... the simplist answer is usually right...

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"Well," the signmaker said, "my pricing is based on which letters you use. Some letters are quite pricey, while others are absolutely free.
For example, the letter A costs two dubloons, B costs three dubloons, C costs three dubloons,
D costs one dubloon, E costs two dubloons, F costs one dubloon, G costs three dubloons, and H's are absolutely free!
But I'm sure you don't need me to list off all of them. Still, the most expensive letter is only eight dubloons.
And don't forget, the price of the letter Y recently went up."
Cap'n Threelegs commissioned the sign to be made, and handed the signmaker a one thousand dubloon coin to pay for it.
How much change should Cap'n Threelegs receive?
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OK... I'm thinking what I have bolded is the key to the solution... think about it this way... this is a children's riddle and like I mentioned, 9 times outta 10, the answer is usually very simple....

Think of the sign as a letter.. not a character, but a letter you write... Still, the most expensive letter is 8 doubloons... meaning he gets 992 doubloons change.