My biggest annoyance, apart from the obvious lack of systemd, was a social one: Any time I had to look up how to accomplish some non-trivial task I would inevitably find a thread on the FreeBSD forums by someone else who has had exactly the same problem in the past, together with a response by some dev along the lines of "why would anyone ever need to do that?".
This is the principal reason why I've leaned toward Debian stable (which also aims at being a stable UNIX like FreeBSD) for decades, even though Debian has also been infected with systemd and has made other questionable decisions. Alternatively, I've also had good luck with Void, Alpine, and Artix. (I've had difficulties with electron apps on Void desktop, but it runs flawlessly on servers.)
either that or "don't do an upgrade, build new ones and replace the old ones instead"
If by any chance it was related to sound, today is your lucky day as I just solved that this morning before work.
Ansible, SaltStack, all the devops automation stuff is available and can certainly handle "freebsd-update fetch; freebsd-update install; reboot".
That was your mistake. With BSDs, you use the man pages ;-)
I don't think this has anything to do with graduating from berkely, I'm a hobo with a keyboard.