The achievement was tested and works. It is in opposite to my original information not required to pay the tax in a single transaction. (Sorry for that!)
The achievement is based on the value of the currency, though. You need to pay taxes equal to 1,000 of a currency's backing item, not just 1,000 currency. That means if the currency you try to achieve this with is backed with 1 iron bar = 1000 currency, you need to pay 1.000.000 in taxes. If it is backed with 1 iron bar = 1 currency, you need to pay 1.000 in taxes.