An adaptive computerized system of assessing the taxability of goods or services sold at retail or wholesale. The system has the capability to conduct an analysis of all products and/or services sold by a retailer or wholesaler and provide the seller with the ability to monitor the tax status and tax rates of any goods or services sold by the seller at the point of sale in any number of taxing jurisdictions in near real time. The system includes a master database which links barcode technology such as UPC to tax assessment information for point of sale goods and/or services transactions made by any number of merchants in potentially unlimited taxing jurisdictions. The master database can modify its own content and that of the merchants' databases to reflect any additions of newly offered goods or services, deletions of goods or services no longer offered, and changes in tax status or tax rate of goods or services still being offered for sale.
