ANSWERS: 3
  • It would not change the amount I give. I give to all sorts of charities that will help them, and I will buy them a meal, but I am not putting $ in their hands. I am too afraid they will spend it on booze or drugs.
  • How could you prove how much was given to the Homeless person to the satisfaction of the taxman. I do not think it would help at all
  • As the resident tax expert, I'm with Firebrand on this one. The IRS would want signatures, forms in triplicate and an agent present at the donation event who would take photos and record affadavits. And the IRS would likely exclude as unreasonable donations over $100. And if you get a pencil or a window-wash for the money, you can't deduct any of it. Even if you paid the guy to stay away from your car, you're giving him money for a service... All that hilarity aside, the concept of motivating with carrots and sticks has been an effective strategy for millennia. But I do know that few people besides the absurdly wealthy consider the tax consequences of their everyday actions. That's why people like me get to dive into shoeboxes of tax receipts this time of year.

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