I use watchtower to auto update everything.
Anything that needs a specific version for compatibility (Postgres mostly) is pinned to the major release.
Stuff occasionally breaks, but I have backups for that reason (if you don’t, set that up now before anything else, they should be running daily at least and you should have 2 types of backup minimum).
Sure:
Proxmox backs up all my VMs/CTs nightly to the proxmox backup server I run as a VM with an external HDD attached to it. This keeps around 30 versions with a retention policy so I can go back pretty far if needed. These are full bootable images and include everything.
Restic (using Backrest to manage it), runs on any VMs/CTs with critical data, and backs up to Backblaze B2 every night as well, this is a more limited choice of the critical files that I’d need. Similar retention policy as the proxmox backup.
With both I try and do some full restores every month or two and test things out.