Error 0x800f0805 is often related to an update servicing or component store issue. Since you're on the ESU program and Windows is otherwise working, I wouldn't jump straight to a reinstall.
First, confirm that the ESU license has activated correctly and that the required servicing stack updates are already installed. Then try running:
DISM /Online /Cleanup-Image /RestoreHealth
sfc /scannow
After both complete, restart and check for updates again.
If the same KBs continue to fail, try downloading and installing them manually from the Microsoft Update Catalog. The installation logs in Event Viewer and WindowsUpdate.log may also provide a more specific error than 0x800f0805.
As for speaking to a human, Microsoft Support should be able to review your update history and ESU entitlement directly. Given that multiple update attempts are failing, it may be worth escalating through support rather than repeatedly retrying the installation.