'Nonprofit organizations, accredited educational institutions, and government entities based in the United States'
US only...
US only...
1 - Bob wants tax deductions. Bob decides to sell pencils for $50k each. Bob discounts them to $0 for non-profits. Can Bob deduct $50k per pencil, for each sold to a non-profit?? Maybe Bob can only deduct his cost, or something?
So in your example, yes, Bob could only deduct the cost of the pencils, not his inflated "value".