Please see below answers to your question.
- Why is my cancel date being read as a text string? -- Right click on data source and edit it. In the Data View area chnage the data type to 'Date' for the column Cancel Dte.
To get the desired outcome you need to use Pivot functionality. Select Cancel Dte Member Enroll Date columns only in the Data preview area and right click and select Pivot. Once you pivot the data see the attached packaged workbook and check if you get the desired results.