I have a user who is requesting an unusual (for us, at least) system of notifications for a new project. In addition to sending emails at specific points in time (e.g. when an issue is 60, 45, or 30 days from its due date) he also wants them sent to different users.
60 days - send to assignee
45 days - send to assignee and assignee's manager
30 days - send to assignee, manager, watchers, and a couple of specific users
I think I've figured out how to use filters and subscriptions to have a notification sent to the assignee when those thresholds are met but don't have any idea how to add the other recipients since some are dynamic.