Other solutions might be easier to deal with this kind of challenge. For example, the Bridge Operator Console is licensed on a concurrent user basis. No need to worry about which PC, etc. It's a much easier process than named user licensing.
Chad, Microsoft has changed direction on their O365/Skype for Business path. They are now working to integrate Skype for Business functionality into Microsoft Teams. There are no API's, etc at this time for ISV's to work with.