So just one contrary question.
Seems like the work flow you’ve outlined relies on software that is available cross-platform: Office 365 has strong Windows and Android apps.
If you were making the IT decision for your institution, would you still choose the iPad Pro for all users? I understand your use case is more skewed towards handwritten input vs more text-heavy courses like language, economics, or philosophy. Wonder if your hardware choice would change in those circumstances to a detachable, or even a touchscreen laptop?