It doesn't matter if you upgrade Docker or not. All tech, self hosted or not, fails for three reasons:
1) You did something to it (changed a setting, upgraded software, etc.)
2) You didn't do something to it (change a setting, upgrade a software, etc.)
3) Just because.
When it does you get the wonderful "work-like" experience, frantically trying to troubleshoot while the things around your house are failing and your family is giving you looks for it.
Self host but be aware that there's a tradeoff. The work that used to be done by someone else, somewhere else, before issues hit you is now done by you alone.
And if you're security conscious like me and want to do things the "right way" just because you can (or should be able to), you now have to think about firewall rules, certificate authorities, DNS names, notifications, backup strategies, automating it in Ansible, managing configs with git, using that newfangled IPv6, ... the complexity piles up quickly.
1) You did something to it (changed a setting, upgraded software, etc.)
2) You didn't do something to it (change a setting, upgrade a software, etc.)
3) Just because.
When it does you get the wonderful "work-like" experience, frantically trying to troubleshoot while the things around your house are failing and your family is giving you looks for it.
Self host but be aware that there's a tradeoff. The work that used to be done by someone else, somewhere else, before issues hit you is now done by you alone.