I am working on a NAV2018 to BC18 conversion for a client for OnPremises deployment. The deployment worked flawlessly when running on a test server, but failed when we tried to do the production system upgrade. Not sure what went wrong, but at the step when we try to run the Upgrade function, it errors out with the following:

Note, it doesn't seem to uniformly fail at the same exact place, but it always fail with the task relating to the four new columns created in 2020 wave2 plus relating to these fields.
We have attempted to restart the process several times from the NAV2018 db and it keeps failing at about this stage of the process. Timeout for SQL commands has been increased from 30min to 4h just in case.
OVerall the upgrade task fails at 58-65%.