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IsSupervisor is a boolean attribute that lives on the System.UserGroup object, which is a many-to-many linking object, so you're likely to struggle to get the value for the right UserGroup record in a value type.
It really depends what you want to do with the data. Am I right in thinking that you only want to notify the supervisor of a particular group as opposed to every member of the group itself? If that's the case, using the "IsSupervisor" attribute may not be suitable for you, because you could have multiple users set as the supervisor for a particular group.
I've worked around this using a different method - we added managers to the group window and added the appropriate people there. It was to allow to send notifications to specific people around resolution times / breaches.
Thanks, good to understand the IsSupervisor a bit more.