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Deductions & credits
It really depends on the auditor.
The rules for donations under $250 and between $250 and $500 are really the same, except for the requirement that the charity indicate on the acknowledgement that the charity did or did not provide goods or services in return for the donation, and for the removal of the "unattended" rule. The real problem is that a charity will almost never issue a receipt that actually complies with the requirements. They give you a blank form you can fill in, or staple to your own written inventory. If you fill in their blank form, but they don't sign it, an auditor could say that's insufficient proof because you might have filled in anything later. If you staple your inventory to the blank receipt, an auditor could say that doesn't prove you donated those items on that day to that charity, you could have stapled anything together.
If you really want to follow the rules to the letter, you need to fill out the blank receipt with your list of items and then get it signed (or signed again) by a responsible person (who might not be the loading dock attendant). The charity will likely not attest a specific value, but that's ok as long as you have an independent method of determining the value and you keep those records with the signed receipt.
So it really depends on the auditor. They are human too, and they have some leeway. If your records are generally in good order, they are more likely to overlook one or two missed signatures. If your records are sloppy, they are more likely to nitpick them and deny everything you can't prove.
But yes, for donations over $250, the rules say that the receipt from the charity should include a description of the items--there should be some way that the charity agrees that the items you claim were donated, really were donated. They sign your list, or they produce a list of their own for you. But a lot of charities won't do this.
The interpretation of the over/under question is also tricky. If you make 20 donations of $200 each, a few days apart, and it looks like you were doing that intentionally to stay under the $250 limit for a more detailed receipt, there are some circumstances where they could deny that on the basis that you deliberately skirting the rules. But again, it depends on the particular auditor, assuming you are unlucky enough to be audited in the first place.
Deductions of Less Than $250
Except as provided below, no deduction will be allowed for a noncash contribution of less than $250 unless you get and keep a receipt from the qualified organization showing:
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The name and address of the qualified organization to which you contributed;
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The date and location of the charitable contribution;
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A description of the property in sufficient detail under the circumstances (taking into account the value of the property) for a person not generally familiar with the type of property to understand that the description is of the contributed property
If it is impractical to get a receipt (for example, if you leave property at a charity’s unattended drop site), you may satisfy the substantiation requirements by maintaining reliable written records for each item of the donated property.
Your reliable written records must include the following information.
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The information in (1), (2), (3), and (4) above.
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If you claim a deduction for clothing or a household item, a description of the condition of the clothing or item.
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The FMV of the property at the time of the contribution and how you figured the FMV.
If you claim a deduction of at least $250 but not more than $500 for a noncash charitable contribution, you must get and keep a contemporaneous written acknowledgment of your contribution from the qualified organization. If you made more than one contribution of $250 or more, you must have either a separate acknowledgment for each or one acknowledgment that shows your total contributions. See CWA, earlier.
The acknowledgment must:
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Be written.
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Include:
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A description (but not necessarily the value) of any property you contributed,
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Whether the qualified organization gave you any goods or services as a result of your contribution (other than certain token items and membership benefits), and
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A description and good faith estimate of the value of any goods or services described in (b). If the only benefit you received was an intangible religious benefit (such as admission to a religious ceremony) that generally isn't sold in a commercial transaction outside the donative context, the acknowledgment must say so and doesn't need to describe or estimate the value of the benefit.
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Be received by you on or before the earlier of:
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The date you file your return for the year you make the contribution, or
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The due date, including extensions, for filing the return.
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