Just updated a server I hadn’t touched in over six years from Ubuntu 16.04 → 18.04 → 20.04 → 22.04 and it all went smoothly; not a single issue.
I can’t wait for a server with Fedora Silverblue-style upgrades (CoreOS?) that’s supported by the major VPS providers in default images. Tried a while back to get Hetzner to support CoreOS but the process appears somewhat stuck: