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Now that we are a 501(c)3 charity organization, I am getting this question a lot. I hope this answer helps.
Any expense that you pay that you wouldn’t normally pay out, as in shipping coupons to military families for Coups For Troops, you can track the amount paid in postage and record it as a tax deduction. My understanding is there is no receipt from us that is necessary for postage.
Regarding the coupons, they are of no value until they are redeemed. Therefore, we can’t estimate the value of the coupons as they are being shipped. What we can do is issue a receipt that states that we received X lbs of coupons (weight) with a disclaimer that estimated value is the responsibility of the donor. In that case, you would be responsible for determining the value of the coupons you sent and if the IRS decides to audit or question the donation, you would be responsible for providing the justification of those numbers.
However, in that case, we would have to track the weight of the coupons that are received. Unfortunately, I fear that would result in losing some of my volunteers handling the coupon donations, because weighing each package and recording the donor’s info would ask another task. However, if you mail directly to a military family, not a satellite location, then your USPS receipt combined with a dated email/letter for the donor receiving the package, should serve as documentation, and then, I can issue a receipt based on the weight shipped, but it would not based on a cash value.