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Invest in an index fund. Every few years (bunching donation deductability as per TTT's answer), donate the appreciated investments. You will be able to deduct the entire value at time of donation from your taxes. If they haven't appreciated, you can either wait longer for them to appreciate, or sell them, take up to $3000 the loss off your taxes, and donate ...


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I would recommend reading this article "How to give like a billionaire" it has some interesting suggestions including how to set up a small charitable foundation which allows you to cash out your equity without the associated capital gains. I'd also recommend avoiding attempting to invest in real estate unless your goal is to use this as a charitable ...


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To add a bit to what Charles Fox has written: Lend the money to yourself for your retirement. In other words put the money into whatever vehicles you would normally use to save for your own retirement. Keep a note of how much of it you would like to have donated, and when the tax laws change in your favour, simply take money you would otherwise have put in ...


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tl;dr: Your idea is mathematically a good one, but maybe you still shouldn't do it. I believe you're on to something with postponing your charitable donations, but for a different reason than you're thinking. It sounds like the change in the standard deduction from 2017 to 2018 affected your ability to deduct donations (as it did many people), since it ...


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