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Instead of multiple contexts, I would suggest less contexts.

The tool, in this case, isn't broken it is the users who need tag things up and down the street to feel productive.

Multiple contexts would just create more cruft and barriers to entering data, as you would have to choose one of many things and spend more time entering a future task than doing it.

If you can do a task in more than one place, great... create a Perspective so you can see both tasks. If you are breaking things down too granular, try easing up on yourself and not use contexts for a week. Your work will still get done. Trust me.

After the week, come back and blow away half the contexts you have, rename a few and move on with your life.

BZ