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When this has been tried before the experts have told congress that it is impossible to write software to keep track of the thousands and thousands of different levels of taxes that would need to be collected. On just one transaction in your own state you might have to keep track of State sales tax, county sales tax, local sales tax and city sales tax. On top of this noone can keep track of when taxes change.
A lot of online business are mom and pop business run out of someones back bedroom. If software could be written to handle this it would cost too much for a small business to afford.
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