As a sort of aside: Is it possible to accomplish the same in Bento? I would like the integration with Mac applications; however, such integration is not necessary.
All of what you describe can be done with Filemaker.
One approach for option 1 is to use a script that runs automatically when you first open the file each day to search for all monthly invoices that need to be sent out that day. There are other options that are also possible for such scheduled events.
The sidebar on the 'Recurring Invoice items' page furnishes data and connections to perform activities on the repeating receipt. Interfaces for altering, ceasing, erasing and making a receipt are accessible on the sidebar. You can see the status and the aggregate of every last one of receipts produced dependent upon this repeating profile on the sidebar.
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