The stuff with licenses Apple likes is relatively up to date; it's definitely not bleeding edge, but no worse than you'd get from Debian or RHEL. The criticism macOS gets for shipping ancient software is because one of the licenses they don't like is the GPL3. So there's a GPL2 version of bash from 2007, rsync is from 2006, etc. The end user can, of course, install newer versions of these separately.

The FreeBSD and *BSD parts of XNU are ancient, which is what I'm referring to, as is some of the userland.

It can't be that old considering they even have pf.

I'm looking at it from the perspective of XNU. Most of FreeBSD's interesting and modern features are not in its userland, but in its kernel and/or exposed to the userland from there. The BSD parts of XNU are literally decades old, and were lifted before jails were a thing.

jail(2) and jail_attach(2) pls.

Also looks like macOS still supports union mounts and chroot.