We had similar problems with update iOS on school shared iPads with Meraki management.
On iPads with OS 13.3, 13.5 update works and goes to latest 14.2.
On iPads with OS 12.1, 12.2, 12.4 update not work (pending or success but nothing happen).
I tried restarts before update, try update more times, nothing help.
Maybe it could cause splitting from iOS to iPadOS?
At the end I used Apple Configurator 2 on Mac to directly update OS via cable.
It works quickly without problems.