Thanks for the detailed information.
Your scenario makes sense to us but unfortunately this functionality has not been scheduled for any specific release yet. I have added one more vote for it to higher its priority when planning future releases.
In the meanwhile you could also use the tagging functionality to get multiple users emailed on item change.
For example, if you add tag with the name of the user interested in the work item - that person could filter the backlog by his name and subscribe for email notifications for each item. I know this solution is not perfect, but could do the job until we come up with a better solution.
the Telerik team
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