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You mean when you update the kernel? No one updates init on BSDs. This is mostly a entire world upgrade. But I’d never reboot from cron. My servers run 100 days without a reboot on average. In most cases there is no reason to update world, only the packages.
Keeping your kernel updated is definitely recommend
Of course, but I can see and understand what is patched and can see if I’m affected or not. In the previous version I haven’t been affected for 500 days.