If I have a repeating rolling task with both a start date and due date of today what happens to the start date if it rolls over to tomorrow? Will the start date remain as today? If it does what happens when I finally check the task off? Will the start date and due date no longer be the same day for remaining rolling tasks?
The start-date and due-date of a repeating task will be moved forwards by the same amount whenever the task repeats. You can test this for yourself by making a fake task if you want to see exactly what will happen for your particular setup.