I've been working on improving the current process of enrolling our iPads into Jamf Pro using Configurator 2.
I've gotten to the point using Content Caching where I can successfully run a Configurator Blueprint which contains what I believe to be the correct shared supervisor, certificates and profiles to enable this to occur.
When the iPad is connected to the MacBook I Apply the Blueprint which applies I can see it Supervised by Configurator, Jamf Pro has it Managed, Supervised using an Enrollment Profile.
There are still 2 pending Commands in management history 'Update Inventory' and 'Install Self Service Web Clip'. Nothing I deploy though Jamf Pro eg "Shut Down Device" as any effect. This is true whether it's plugged into the MacBook with Content Cache on or connected to WiFi.