Debian upgrades "just work". Even had colleague accidentally upgrade 2 releases at once (put too new repo on one of the old servers) and it worked without a hitch
Ubuntu? eh, usually ?
CentOS/RHEL/derivatives ? It isn't even supported as a feature.
Both my desktop and NAS are going 10+ years with just dist-upgrade. Also few hundred servers at work where we migrated from CentOS (which was a chore to manage tbh).
As both a Debian and FreeBSD person, I think I was uniquely in a position to like this, and it was awful circa 2012. Some stuff would work, and a lot of stuff didn't, because FreeBSD basic utilities weren't packaged and GNU versions didn't have full functionality: network configuration was difficult, lots of administration was also difficult. You ended up needing a FreeBSD chroot, and then you might as well use FreeBSD/FreeBSD.
But I use configuration management anyway to keep the machines consistent, and, well, upgrade is less work than reinstall... especially if talking hardware that can take 5+ minutes just to reboot (which is like every actual enterprise server I saw).