In the edit task menu, I think there could be a better use of space and faster experience: i.e. why not have the roles dropdown appear from the start? It would take up no more space and eliminate a click of having first to select "choose a role"

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You can assign a role by mentioning it in the task text "Remember the milk @Home" for example.

Because there are multiple ways to add a role, I thought I would not give as much priority in the Edit dialog because there are so many other fields in that dialog already.
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