I love this idea! Depending on your situation, it’s possible to get the ability to itemize all by yourself, by saving up your donation amount on certain tax years. For example, Bob could hold on to 10k for two years in a row, then donate 30k all at once, to clear the 12k bar for itemizing. I’ve done something similar when for years when I expect my income to be lower (if I plan to leave a high paying job in a year, then perhaps I could donate extra now and do less next year for the tax advantage).
One downside is that Bob’s marginal tax burden is lower than Alice’s (maybe 25 percent rather than 40 percent), so having Alice donate is still more effective. But this way Bob avoids the need to coordinate with another person. Of course, coordinating could be a benefit in and of itself!
I love this idea! Depending on your situation, it’s possible to get the ability to itemize all by yourself, by saving up your donation amount on certain tax years. For example, Bob could hold on to 10k for two years in a row, then donate 30k all at once, to clear the 12k bar for itemizing. I’ve done something similar when for years when I expect my income to be lower (if I plan to leave a high paying job in a year, then perhaps I could donate extra now and do less next year for the tax advantage).
One downside is that Bob’s marginal tax burden is lower than Alice’s (maybe 25 percent rather than 40 percent), so having Alice donate is still more effective. But this way Bob avoids the need to coordinate with another person. Of course, coordinating could be a benefit in and of itself!
Relevant forum post: https://forum.effectivealtruism.org/posts/MAod5gvcQgdxaXdWA/long-term-donation-bunching