My approach to this would be entirely aligned with how the business has laid out it's IT strategy. You've also already told me that the stance is not to be 'bleeding edge' so, if you're telling me that the business has only now gone to v1909 in October & November of last year, I wouldn't be suggesting that 'we' consider the upgrade again until at least 12 months following. In that time, I would encourage us to develop a build which incorporates key business applications using the next intended major version of Windows 10, working with it within the department and then form a pilot; branching it out to key stakeholders to ensure it's robust enough and ready in plenty of time for rollout before the end-of-life date for 1909.
Again, briefly (and from what I can recall): - Is the SCCM client on the machine healthy, operating and correctly connecting through it's management point to receive policy updates? - Is the content for the deployment accessible to the client - is it connecting back to the environment via a route through which it can communicate (at least) with an SCCM distribution point which holds a copy of the package content? - Is there enough disk space on the machine for it to cache the content prior to execution - Is the WSUS agent on the machine functioning correctly - are there any errors reported in Event Viewer which would indicate that it needs repaired or there is a larger issue with the OS on the machine?
The questions are far from the norm, don't expect typical competence based, its all about you. Apple will train you and mould you the way they want anywho, I like to think of this as being "Apple-ised"