First off, yes it’s a pain in the ass in practice and a real headwind for using crypto as a currency. At the same time most people are treating crypto as a prop

First off, yes it’s a pain in the ass in practice and a real headwind for using crypto as a currency. At the same time most people are treating crypto as a property investment in practice, so it’s hard to dispute the IRS’s approach here. As for solving the problem with software, it’s already “solved” by your broker. In the investing world when you sell you choose which lots you want to sell. You typically tell your broker what sort of strategy you want to use (LIFO vs FIFO) and they handle it for you. So I’d expect a software solution to work the same way - you would configure the software to LIFO/FIFO/other.