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Or do like parking lots. If you lose the ticket they assume a worst case scenario and charge you a lot.

If you can't keep up with the records, then you should assume the basis is $0 and pay taxes on the whole sale as profit.

Then people would take the time to track it.

Part of the problem is people underreport their gains. While the parking lot idea would help, it would still require auditing with fine and penalties for underreporting, which in itself would be a big deterant.

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