What challenges does Jackson face in trying to get the $999 dollars in "What You Pawn I Will Redeem"?

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In "What You Pawn I Will Redeem ," Jackson is challenged by his own character traits and flaws when trying to earn the $999 that it will cost to buy his grandmother's regalia from the pawnbroker. For example, at one point along his journey, Jackson wins $100 from a lottery ticket, but...

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