Virtual network for a bunch of jails with nat. I wanted exposed ports on the host machine mapped to a reverse proxy jail that did tls termination before forwarding to other jails on a virtual network (while allowing the jails on the virtual net outgoing internet access).
Several applications that were apparently built for Linux, so they did not compile on Freebsd (and no alternatives available).
Getting newer versions of software. Often the version available in pkg is several major versions out of date.
Documentation for how to do things in general. Yeah when there are docs/tutorials they can often be of high quality, but frequently there is just nothing or the available docs does not cover the edge case you are trying to solve.