Yeah, I ditched Ubuntu Server after too many upgrade headaches. I manage 75+ VPS instances for app hosting, and it's nerve-wracking doing maintenance updates knowing there's a chance one won't boot after. That's easily an extra 1-2 hours per VPS just to get it back. Switched to Debian back in the 8.x days in 2015 and it's been smooth sailing. Never had it break unless I was the one who messed it up.