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OmniFocus is a great product, among others because of its excellent usability.

There is, however, one thing which is not intuitive at all: repeating items (actions or projects). Yes, the feature exists; yes, many people seem to be happy with it, but :
  • Setting up repeating projects is complex.
  • Many threads in the forums are about repeating items.
  • There are also many help pages / blogs about this, with explanations on how to achieve specific needs.

Why is it so complex ? Why is the user interface for repeating items so complex ?

I think the reason is that OmniFocus, like most of the similar tools, doesn't make a clear distinction between repeating action definitions (where you define when and how an action shall be repeated) and repeating action instances (the actual actions to perform).

Hence, a cleaner solution would be to completely separate definitions (located e.g. in a specific folder like "Repeating items") from instances (located in the regular project folders) in OmniFocus user's interface.

Advantages of this solution :

1) When the user modifies something, he clearly sees whether he is modifying the definition or an instance of an item, thus reducing the need for confusing questions like "Do you want to modify this event, all events or only future events ?".

Same thing with deletion : you clearly know whether you delete the definition (thus preventing the creation of future action instances, but leaving existing one(s) untouched), or you delete an instance (which doesn't change the definition).

2) Start and due dates are finally easier to set up (it is a mess today) :
  • In an action definition, all dates are clearly relative dates, relative to the start date. The "completed" date is not present (it is meaningless).
  • In an action instance, all dates are clearly absolute dates.

3) Repeating actions can have a cleaner naming scheme :
  • The definition of an action is named for instance "Monthly report".
  • The instances can be automatically named "Monthly report - January 2011", "Monthly report - February 2011", with hence a more meaningful name.
  • This is very useful if more than one instance is active at the same time, like e.g. when you come back from holidays and are three weekly reports late : "Weekly report - Week 33", "Weekly report - Week 34" and "Weekly report - Week 35". You can then decide for instance to delete the weekly reports 33 and 34, and just keep 35 due.
  • If the action is created in "Start again..." mode (like e.g. for a haircut every 2 months), the definition would be "Haircut" and the instance "Haircut - due January 12th 2011".

What do you think ? Do you also have issues with repeating items ?