I would write an editor extension and have both the toolcontrol (with the checkbox) and the edittask talk to the edit extension to decide how to behave. The extension would not be aware, however, of the toolcontrol or the edittask - if it needs to be notified then use events.
For example, if the edittask needs to know that the checkbox has been checked/unchecked while it is the current task, it would subscribe to a checkchanged event which would be raised by the edit extension whenever the Enabled state is changed (possibly - but not necessarily - by the checkbox on the toolcontrol).
Wiring all these notifications can be a bit daunting. Silverlight/WPF provides a much cleaner way of doing this (through XAML and INotifyPropertyChanged) , but haven't looked into using it with editing events. I suppose there would need to be a WPF based toolbar? Anyway, I would be interested in seeing an example using WPF to write controls that support this scenario.