I try to set aside time to do maintenance once or twice a week. I do a backup of my system using the standard backup tool then do the full upgrade of everything, starting with all the HACS and Addons, then the core OS stuff, then reboot. Then I test a few things and make sure it looks OK. I haven't had any issues yet but I know it is a matter of time. I have a second computer I will be testing restoring onto shortly, so I will make that part of my process. No point having a backup if you haven't tested it.