Comment by distances
Yes, dist-upgrade was the biggest pain with the Ubuntu based KDE neon too. I'd wait for multiple months after a new version was published before I'd upgrade, and still would often encounter issues that broke the boot. I made sure to reserve at least half a day for each dist-upgrade -- multiple times I fixed issues with a bootable USB image and mounting the full-disk encrypted partition to fiddle something.
I was always able to recover with some insights from random forum or Reddit posts, but I can't say this was the type hacking I wanted to do.
I'm hoping a rolling release is easier in the long run, but we'll see. Also this time I used a separate SSD for /home so that at least I could do a full reinstall and still keep my data.