To expand: the more a stock has grown since you got it, the higher the tax advantage, because you get to deduct the full market value, not the cash you're left

To expand: the more a stock has grown since you got it, the higher the tax advantage, because you get to deduct the full market value, not the cash you're left with after capital gain taxes. So pick your lots carefully. Also, if you know in advance your income will be higher than in the future (one time events, etc.), you can transfer the shares now, invest the cash in the fund as you see fit and distribute it over the following years. Another practical benefit is that it allows you to make small donations to tens of nonprofits without fearing you'll be drowning later in fundraising letters, by virtue of not passing your home address along.