We have extended the measurement of content complexity to a practical level by developing a model for evaluating a particularly complex body of information: the federal income tax laws. United States tax law has been seriously criticized as being overly complex, and the capital gain or loss tax preference significantly contributes to this complexity. By developing and applying a content analysis measurement model, we have determined that over 15% of the tax law's complexity is attributable to the capital gain and loss preference and that this preference affects 65% of all income tax sections. The consequences of this complexity are currently an unresearched area. The findings confirm the hypothesis that the capital gain and loss preference substantially complicates the income tax law in both absolute and relative terms.