… how to safely update the system (regardless of how far out of date) reliably. …
Let's assume that PkgBase is the way forward.
<https://alpha.pkgbase.live/> and so on.
https://lists.freebsd.org/mailman/listinfo/freebsd-pkgbase
In addition to the list, there's sometimes discussion of PkgBase in IRC for FreeBSD.
Retrospective (2018–2019)

Solved - What is Pkgbase?
Could someone explain what is pkgbase, which problem it is going to solve, and (roughly) what will be its capabilities? I have read this page but unfortunately it is more like an implementation tracker than a wiki explaining the role of pkgbase. I feel like if you do not already know what...

Call for Testing (CFT) for FreeBSD + ZoL and Pkgbase
Kris Moore, FreeBSD contributor and spear-header of the ZFS on FreeBSD project, announced a Call for Testing of the latest development built on FreeBSD 12-STABLE. You can download the ISO from the link below. In other recent news, a TrueOS inspired package base for FreeBSD has also been uploaded...

pkgbase instructions?
These are the instructions for pkgbase? https://wiki.freebsd.org/PkgBase just relate it to 12.0 releng, instead of head. cd /usr/src make [make flags] buildworld make [make flags] buildkernel make packages /usr/local/etc/pkg/repos/FreeBSD-base.conf # FreeBSD base system repository...