https://github.com/freebsd/pkg/blob/master/libpkg/repo/binary/init.c#L334 makes me notice pkg wasn't invoked as root.

https://packages.nasqueron.org/freebsd/ works fine

I have no idea how to do it, but looks like a good plan. Apart that, in my opinion, you do a much more of what would be necessary to run nasqueron services (but it is your time, you use it like you want)

Those are valid concerns.

looks an interesting tool, something quite frightening is that it comes with a set of exploit, (if I understand, a common way to exploit sudo flaws).
As a shell script not even indented, it is absolutely unreadable, and more or less one have to trust the creator to not making mistake.
Moreover for full use, you have to give a sudo password in clear text ( I just don't understand the reason)
As such, I would say it would be kind of crazy to run it automatically and I would not comfortable to simply run it for myself in any way.

Tagging security as we could need follow-up ACL to allow to connect to.

looks ok

I wanted a test to detect the case, but it's not trivial, as we currently don't have a sls renderer.

s/os/osfamily

It's provided by PSmisc.

Temporarily hotfixed with ln -s /usr/local/lib/libreadline.so.8 /usr/local/lib/libreadline.so.7

Already submitted and merged as D2056.