Probably Debian or Ubuntu. The question is...why do you care that much?
I've upgraded Debian stable (both pure and with some cherry-picked backports) and Ubuntu (non-LTS and LTS) systems in place and rarely broken anything, for years and years. When stuff has broken it's been a quick google and then slapping myself for not having read the upgrade guide.
I do generally wait about 2-3 weeks before upgrading, giving time for them to catch stuff that was missed until the great masses were set loose on it.
> The question is...why do you care that much?
Not the OP, but I support Ubuntu as desktop and server OS for an engineering collage and have for 10ish years. Some LTS upgrades don't require many changes (mostly minor package name changes) and some take months of work to get rolled out (mostly for workstations, the server upgrades are usually quick.). Not everything gets upgraded every new OS release. If we had to upgrade everything every 6-12 months it would eat up a significant amount of time for our small team.
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.
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.
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
> why do you care that much?
I've had issues with Ubuntu/Debian upgrades more than once. Some third party binaries breaking with the update. Or some specific config tweaks that break, because the structure of /etc changed too much.
For some small VM with a specific purpose I prefer a distribution that changes as little as possible for as long as possible. Less work, more uptime.
I won't touch ubuntu unless forced to by some obscure work requirement. I've had enough bad experiences with repos being shut down, updates/upgrades breaking unanticipated, obscure things, and I hate snap.
The naming conventions drive me crazy as well. When you deal with 2 things that have dumbshit naming conventions, like ubuntu and ROS, its really obnoxious to pretend to case enough to keep track of.
Ive had nothing but issues doing that. I think I’ve had a Debian upgrade actually succeed maybe one time? (After some manual intervention to fix some issue other booting on my work server)
For updates, Debian and Ubuntu are great. For upgrades… not so much for me.
I had unattended-upgrades cripple our VMs