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> Ubuntu generally necessitates a re-install between releases.

What? I have taken fossilized servers neglected for ten years and managed to successfully get them to 16.04 LTS - stuff is harder with Debian where e.g. mysql-server has disappeared in buster and replaced by MariaDB.

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It is possible - but officially discouraged - to do a dist-upgrade on Ubuntu. Sometimes it works, other times it 'almost' works. It is the latter problem which makes the official discouragement a reasonable precaution against breakage. Things like the mysql->mariadb migration in Debian might necessitate manual intervention but this is made clear from the onset.

dist-upgrade is discouraged on Ubuntu for switching releases because there is a supported tool for the same purpose called "do-release-upgrade".

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