If there was a current port of Docker for FreeBSD and Wi-Fi ac support, it would totally be my daily driver right now. Currently I still use Gentoo on my laptops.
Not saying you'd want to do that, but my understanding is that this is part of a lot of the clever networking you see in orchestration systems.
I haven't had a need to have a jail inspect traffic of another, I suspect that might be tricky. However I've used them successfully as a lightweight alternative to a vm for QA/dev environments -- use hard links for the base OS to save space, and give each jail its own ip and you get fairly cheap multiple boxes. I've also used it them to contain statically compiled binaries -- TLS terminator runs without access to much of anything, if the next vulnerability after Heartbleed was worse, it would be a lot harder to escalate vs common deployment with OpenSSL linked into a webserver; similar with an environment running ffmpeg.
The battery life on my X220 was a solid hour less under OpenBSD than under Debian, and it ran some 10 degrees hotter. Yes, this is post-apmd improvements.
I want to like OpenBSD but code correctness just isn't enough for me.