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Lumifer comments on Things I Wish They'd Taught Me When I Was Younger: Why Money Is Awesome - Less Wrong
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Point being, it's not up to the Rolling Jubilee to decide. It's up to the IRS to decide.
If the Rolling Jubilee wants to be serious about it, it needs to get a Determination Letter from the IRS stating that yes, IRS will treat these debt cancellations as tax-free gifts.
Yup. Have a look at that interview with the top tax lawyer to see how that will likely play out. (Short version: 1. Medical debt is likely much easier to forgive tax-free than mortgage debt. 2. The debt forgiveness is currently so small that it will probably be lost in the shuffle without the IRS wanting to devote resources to making a determination.)
The point of my comment was really that if James_Miller had posed the question out of genuine curiosity instead of as a rhetorical side-swipe, he could have found the answer.