1. If you are over 70 1/2 and you donate directly, it is not considered a distribution for income tax purposes and it counts as part of your RMD. Because it is not part of your AGI, you don't itemize it as it bypasses everything - no income, no deduction. I am pretty sure on this one but I would still verify.

2. If you are under 70 1/2, I do not know if you bypass reporting it as part of your AGI. If you could, this would be better as you would still get the $24K minimum deduction. The real danger is do you get a double duece. Add to AGI and don't get to deduct on your itemized. I don't know, and I know enough tax accountants that I would believe the first guy I talked to.

3. You could take a withdrawal from your 401K and then donate cash for multiple years which gets you to the same place in many ways.

Hope that helps.