Hey, I have a similar problem...
Here's my issue: I am an attorney that needs a good tickler (reminder) system to alert me to one-time deadlines and recurring deadlines. I want to see these deadlines in both a calendar view and a list view that I can sort by next occurrence/appointment.
Here's what I have found:
While I can create a "Deadline" task list that will sort by "Due Date" providing me with the list described above that sorts all my one-time items and recurring items by the next occurrence, it cannot be viewed as a calendar - so no good.
Creating a "Deadline" calendar allows me to view the items/appointments in a calendar view, and I can view these items/appointments in a list view, but I cannot sort the list as I want. In the calendar list view, I can retrieve all calendar appointments that have not expired (including the recurring items) by filtering the "Start Date" for all dates after the current date. However, if I try to sort the list by the "Start Date" field, I cannot sort the recurring items by the next appointment "Start Date," instead the "Start Date" field for recurring items is populated with the creation date (a date that obviously is not be used for the filter described above). So...I thought I'd be tricky and use the "Field Chooser" to pull in some of the task list fields into the calendar list view - specifically "Due Date" so that I could sort the calendar items the same way that I can do with task list items. But even if I add the "Due Date" field, those "Due Dates" are not updated as they are updated for the task list items because the "Recurrence" field for task list items that is used to update the due dates for those task items is not the same as the "Recurrence" field for the calendar items. And even if I use the field chooser to pull in the task list "Recurrence" field, I can't find a way to update the related task list Recurrence fields....
Logically, it seems that an add-in could be created to make the Outlook tickler system I envision by doing any one of the following (1) showing the next occurrence date rather than the creation date in the calendar "Start Date" field - which is clearly picked up by filtering, (2) allowing the user to alter the task list "Recurrence" field data for calendar items so that the "Due Date" field can update to the next occurrence/appointment, or (3) allowing a calendar view for task lists.
Any suggestions?
-JLoomis