Ooooooooooh my lanta. Can I get idiot award of the month please? I didn’t realize Plex needed you to set “allowedNetworks” in the configurations. I honestly didn’t know because it literally worked out of the box on Linux, despite being in separate networks. It works now!! insert facepalm emoji here
FreeBSD people: long story short, you don’t need to use VNET jails to handle broadcasts, if your server is on a separate local network go to “/usr/local/plexdata/Plex Media Server” and edit the Preferences.xml file and add allowedNetworks=“172.16.0.0/28,192.168.10.0/26” with your networks being your respective networks.
I love when the solution is too simple to even consider haha 
