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I have a container running Watchtower and it checks once a week for any updated images so I can go through and update whatever needs updating myself. IIRC there's an option to have it automatically update stuff but I don't know nearly enough yet to be comfortable with that - If something is going to break let me break it myself so I can troubleshoot it haha.
I use Portainer as a GUI docker management system, and in regards to updating I can just hit a "Recreate" button and select "re-pull image" to update them. As long as you have the containers tied to persistent data folders it just pulls the latest image and ""re-installs"" it per your docker-compose file and everything is just as you left it.