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Only using ubuntu rn, but when the server is mostly running docker, it is simpler upgrade nowadays with so little dependencies. But then the problem just moved to the container image updates.
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I have a machine that has been Fedora since twenty-something to current 44, and upgrading yearly is a breeze. Three commands, and just wait for a download and the reboot. The only thing that breaks if you forget that the upgrade needs attention is the system Postgres, until I migrated to Podman images.
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I recently upgraded to Fedora 44 from Fedora 43 and I wouldn't say its a breeze, it can be difficult, especially if you've enabled extra repos.

If you use Copr (Nvidia Drivers, Non-Free Stuff) you need to ensure all your Copr packages work fine in the next version of Fedora. A ton of packages haven't been updated for Fedora 44 and this will cause issues.

The same applies if you use Terra

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