You know they are only twenty bucks a piece. And keep in mind, best thing that happens: you help the homeless and you win a car. Worst thing that happens: you help the homeless and you write it off your taxes.That is awful tax advice and could get someone in trouble with the law. IRS publication 526 makes it pretty clear: "you cannot deduct as a charitable contribution amounts you pay to buy raffle or lottery tickets or to play bingo or other games of chance."
Bob should skip giving out tax advice and stick to what he knows best: demonizing Democrats and pimping for the Republican Party!