During the first upgrade attempt from 7.X to 8.X the errors are received that match KB Error: "Could not authenticate to source appliance OS on address" when attempting vCenter upgrade but when following the resolution steps from the KB they do not resolve the issue.
A retry is attempted by re-entering the OS password using the same installer, the error from KB: Upgrading vCenter from 7.x to 8.x fails with error "Pre-upgrade check failed due the following problem: Error in method invocation [digital envelope routines] unsupported" is received and the resolution steps again do not resolve the issue.
The vCenters version of OpenSSH has been modified outside of a supported method.
As described in KB Vulnerability found for openssh of the vCenter server
If the issues described in this KB are received, then we recommend opening a case with Broadcom Support to confirm that OpenSSH has been modified outside of a released vCenter update or patch.