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He's asked for the tune of $20,000 this year alone.

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Remind your son that grandmas gifts makes her ineligible for Medicaid for the next five years - ask him if grandma can come live with him when she can't afford medical care, since it's due to him.
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Well, if you are his mother, it is not too late to break out the wooden spoon.
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Sorry - assumed son. Should have said son or nephew.
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Yes it can... whomever is the financial Power of Attorney takes over all the finances, pays the bills from your Mom's funds, etc.

Therefore, if grandson wants money, he would need to go through the Power of Attorney, as long as the POA is a no nonsense type of person who probably would say no.
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