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i have just read this thread and my sonwho is nine has problems using a calculator, he forgets what it is he is trying to work out and how he was going to use the calculator.
I think a calculator with a screen that records what you are doing would be very useful. So if he was working out fred has two sweets and betty has one more than fred. How many sweets has betty. His calculator could show his workings.

2
2+
2+1
2+1=3


If we were talking PDA and not calculators he could enter 2 and see 2 dots ( or marbles).
He could enter 2 x 10 and see two lots of ten marblems

Pre programmed questions with require an inserted number could take this format.

What is half of .....? then press enter for answer
What is ...% of....? then press enter for answer

Questions could be upgraded for business to help with tax or VAt. The trick would be to keep the questions in the language that society uses.

Just a thought...