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Answer by gordoni14

A few US-centric notes.

The 60% limit only applies if your entire donation is in cash, otherwise the 50% limit applies.

If you have it, you should probably aim to donate 30% of your AGI in taxable appreciated shares held one year or longer, and 20% in cash. You receive a tax deduction equal to the fair value of the shares, but don't pay capital gains taxes on them.

Donations in excess of the limits can be carried forward for up to 5 years. Although current year donations take precedence over using up the carry forward amounts.

You should donate shares with the greatest percentage gains, and use shares with the smallest gains, or largest losses, for personal expenses.

You should avoid realizing capital gains unnecessarily.

Don't invest in an all in one fund. The more fine grained your assets the better as each asset has separate gains and losses. Although investing in 100 different stocks, as some of the robo advisors do, might be taking things to far.

You should bunch donations in particular years to reduce the dilution of the standard deduction on the charitable deduction.

You can use a donor advised fund to decouple tax management from giving.

At age 70.5 there is something called a Qualified Charitable Distribution from a traditional IRA of up to $100,000 per year. This avoids taxes and counts towards the IRA Required Minimum Distribution requirements.

401(k)'s can be rolled over into traditional IRAs.

If you receive a windfall you should donate substantially in that year in order to reduce taxes.