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Another idea might be to just let people keep their individual databases, but maybe automate the process of sending a daily or weekly status update (say, in the form of a PDF or HTML file) from each worker.

One thing that I would guess to be a disadvantage of assigning tasks like you describe, as I tried to say before, is that different people have different ways of arranging their work. What might be one task for you might be five for someone else, perhaps in the same task group and maybe spread over multiple task groups. Or maybe the task that you assign gets folded into a larger group. It seems to me that its ongoing status at that point starts to lose meaning. Does that make sense? So when a task gets completed, and then that automatically checks off some supervisor's corresponding task, that task being completed might mean different things. I know that you're thinking a lot about this problem, but it seems to me here that the perfect might be the enemy of the good. Just something to consider!