I suppose it wouldn't really be malicious, as the IRS must deal with huge amounts of data from day traders and others who frequently trigger taxable events, but I'm interested in learning about ways people who want to use bitcoin as a currency can automate the taxable event that occurs when they spend bitcoin. I'm picturing an app where I can enter every bitcoin purchase I make and every payment I make with bitcoin so that a report will automatically generate for tax purposes. Does something like this exist?
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