Charitable Contributions of Investment Property
If you make substantial charitable contributions in cash while holding investments (stocks and bonds), consider gifting investments that have increased in value instead of cash. A double benefit results: the gain on the investments is not taxed and the fair market value is deductible. Conversely, if you hold an investment that has decreased in value, you should sell it and give the cash proceeds. By doing so, you can deduct the loss (up to $3,000) and deduct the cash contribution.