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I think Alarms is an essential piece that is missing. It could work like this..

OF could add a checkbox field called Alarm. If you had a time-dependent task, you would check the Alarm box, add a due date/time and it would get added to an OF Calendar. With iCal subscribed to the calendar these items would appear in iCal as 5 minute events with an alarm.

Then you can keep all these tasks in OF, rather than adding them directly into iCal as one-off events. Thoughts?