I skim read the changelogs for breaking changes but mostly just YOLO it whenever I’m in the mood to update or a new monthly release drops.
That said, the VM that runs HAOS and the Z2M addon is snapshotted every night with two week’s worth of retention, and I let HA do its own scheduled backups in case a snapshot restore doesn’t work for whatever reason. So far I’ve never had a need for either but I rest easy knowing the options are there.
Ha, I’ve only ever watched one episode of Always Sunny and it just happened to be this one. How convenient for me!