FWIW, I once abandoned an Ubuntu server for a decade, and managed to update it painlessly in 20 minutes. That same server is still running today, now with the latest LTS. I think I might have even started with Ubuntu 4, or perhaps 6, and it has been painless all the way through. Perhaps my slow upgrades saved me from early adopter woes :).

I use Debian now much more. With all the supply chain attacks, Debian Stable feels like an absolute jewel, even if there are always a few packages I need to handle separately because I want or need a more updated version. But I love the old school no-nonsense engineering ethos.

I have a machine that's on a Debian installation that I've been steadily upgrading, one Debian stable release at a time, since I originally installed it about a decade ago now. At one point I even copied the entire installation to another disk (just a "dd" from its original SATA SSD to a new NVMe one, plus some partition and filesystem resizing), and I've upgraded the CPU/motherboard/RAM at another time, and it just keeps going reliably. It's fun knowing that the origin of that Debian installation predates every hardware component it's presently running on (with the exception of only the case and power supply).