I gave up on updating because the 2 times i updated the HA Core package and the OS most of my integrations broke. The first time i bothered changing the config. The second time I decided to rollback and keep everything as is.
> This is an advanced installation process, and some steps might differ on your system. Considering the nature of this installation type, we assume you can handle subtle differences between this document and the system configuration you are using. When in doubt, please consider one of the other installation methods, as they might be a better fit instead.
I use the container installation method and it's usually as simple as updating the version number in Docker Compose and restarting. I'd imagine the full OS image is even easier and more stable.
> Home Assistant Operating System: Minimal Operating System optimized to power Home Assistant. It comes with Supervisor to manage Home Assistant Core and Add-ons. Recommended installation method.
I tried on purpose to do everything as 'basic' as possible because I don't want to spend time making sure it keeps working.
It notifies you when there's an upgrade, you just click "Install" in the GUI.
That said, every time I update it the disk image grows by like a full gig. Haven't figured out where that's going so I just don't update it anymore. It's running on a minimal headless computer and doesn't have enough space to keep doing that.
Additionally, if you got in ~5 years ago when it was pure yaml, it seems a couple times a year there's breaking changes where more yaml is ripped out and manual reconfig is necessary (it'd be nice if it just migrated the config for you)