[brianogilvie]

Yes. Create your action and select it. In the Inspector, enter a due date of the 5th of the next month and click the check box next to "Repeat every...". In the popup, choose "month" and then select the radio button for "repeat from assigned date."

Now, when you check off the action, a new action will be generated with a due date of the 5th of the following month, even if you don't check off the original until the 9th. (If you chose "repeat from completion date," the next action would be due on the 9th of the next month.)

If you don't want the new action to be available until shortly before it is due, you can also enter a start date. In fact, you can use a start date instead of a due date, depending on your needs.