Question on transition from managing iPads with Configurator to managing with MDM (using VPP)

The upshot is that you have to be able to prove ownership of the devices before they can be enrolled in DEP.

https://www.apple.com/education/it/dep/
https://www.apple.com/education/docs/DEP_Guide.pdf

The most important part is on Page 3, Step 3 (Assigning Devices). The devices have to have been purchased through Apple or an Apple Authorized Reseller who can provide the serial numbers for your verified purchases. The whole kit-n-kaboodle can be uploaded as a CSV.

The rest of the process (designating an administrator, setting up institutional Apple IDs and registering in the VPP) should be a walk in the park (relatively speaking) and can be managed smartly if your organization documents everything and ensures at least 2-3 high ranking individuals in management have copies of said documentation.

I assume by Configurator/VPP you mean VPP codes and will be transitioning to VPP managed licenses?
Yes you are able to have two separate VPP accounts managed from the JSS

One thing to be aware of is every user will be needing their own Apple ID to be signed in and associated with your VPP.

Be aware, when transitioning from codes to managed licenses, depending on your method of scoping you may need to purchase more licenses to cover the users that already have that app, as VPP does not check to see if the user already has the app before designating them a license.

Once your devices are in DEP you'll assign them to a virtual MDM server on the DEP portal. This virtual server will be linked to the JSS, and you'll add them to a Pre-Stage Enrollment. If your iPads are currently Supervised, they will need to be Unsupervised from Configurator (which wipes them), and then during the Setup Assistant they will receive the new Supervision from DEP. This can't be done with an iCloud restore to the same device.

If I remember correctly, Configurator consumes/redeems just the top code of the spreadsheet. You can contact VPP Support and have your codes converted to Managed Licenses. You will need to convert them all, but it does not break existing Configurator workflow nor uninstall the apps in any way, in case you need to leave some shared iPads out there.

Be aware, when transitioning from codes to managed licenses, depending on your method of scoping you may need to purchase more licenses to cover the users that already have that app, as VPP does not check to see if the user already has the app before designating them a license.

Agreed. For example, if you had gifted the VPP codes to your students in the past then you could put them into a User Group and then exclude this from your VPP Assignment.

chris