Upgrade sounds like an inplace upgrade (better do a fresh install on a new machine)
Inplace Upgrade => First problem for you will be... there is no direct upgrade path from 2008R2 to 2019... you have to do it in a two step upgrade process... SQL Server 2008R2 => SQL Server 2012 => SQL Server 2019
https://learn.microsoft.com/en-us/sql/database-engine/install-windows/supported-version-and-edition-upgrades-2019?view=sql-server-ver16
in preparation of that upgrade you might check your environment with Data Migration Assistant
https://learn.microsoft.com/en-us/sql/database-engine/install-windows/prepare-for-upgrade-by-running-data-migration-assistant?view=sql-server-ver16
It might be easier and better to just migrate the databases via Backup/Restore from that old system to freshly new installed SQL Server 2019, here you also can check everything before the migration with DMA.