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You are certainly correct that there would be raised eyebrows among the FA folks if they know the student gave money away. They will only know if I tell them.

I know most of the financial aid directors in my state, although I am not one. You vastly underrate their intelligence and their ability to spot anomalies in financial aid applications. Pell grants are an entitlement program but pretty much outside of that, professional judgement may be used to award or not award aid as they see fit. Playing games, legal or not is often not well received.

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