[krylon]

It's been a long time since I have used Ubuntu. In the ~2009-2013 era, my desktop ran Ubuntu, and I repeatedly upgraded it from 2008.04 -> 2010.04 -> 2012.04. There were a few issues, but nothing that made the system unusable. But that was over ten years ago, I have no idea how Ubuntu has evolved since.

Raspbian has been problematic for me. I tried upgrading from Buster to Bullseye, and it went so badly I ended up reinstalling from scratch. (To be fair, the docs were clear that was a likely outcome.)

OTOH, my ThinkPad x220 has been running Debian since 2016, I installed Jessie back then and upgraded as new stable versions were released. The upgrade to bookworm has finished by now, and it's been entirely unexciting. :-)