Charitable contributions are generally pretty straightforward, but you can get tripped up on occasion.

Remember that only qualified charities count for deductions.  Donating $20 to a family in need or a person fighting cancer is a very good thing to do, but in the eyes of the IRS they’re not deductible.  Typically these events have a sponsoring entity.  The easy workaround is simply to donate the $20 to the sponsoring entity (if they qualify) and specify that it be used for the person being helped.  For example - your church is helping a family that lost it’s home to a fire.  Don’t make your check out to the family, make it to the church and specify that it’s for the family.

Another  point to remember is that cash contributions don’t count unless you have some sort of receipt.

Finally - purchasing a good or service from a qualified entity is only deductible to the extent that the purchase price is greater than the retail value.  For example - you buy a print from Duck’s Unlimited for $250.  The print is valued at $200.  You can only deduct $50.