Hi @Matt Dillon ,
Since your server is a physical server, installing the Windows Server Backup role would be a good idea indeed.
By performing a Bare Metal Recovery (Full backup) you will be able to restore your server in case anything might go wrong during the in-place upgrade, easiest is to back up the server to a network share that is accessible by your physical server.
In-place upgrades are never recommended, although still supported, but for any server, whether it's virtual or physical you should always have a backup.
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Best regards,
Leon