If your using a linux box as you main machine Unix ftw. ACLs seem to complicate things more than they help. Post after post about people with permissions issues.
Create TN user in the host and each jail thats the same name, pass, UID/GID as your linux (or Windows even) user and allow him to own datasets/shares fully and or by group and he also run all addon softwares in jails via jail rc.conf. In the end if you do this you wont be back in here next week asking why you cant move your baby pictures, plex doesnt see your movies or transmission cant download files. People try to get too crafty with users and permissions.
If this is a home use server dont go too nuts on permissions, ive seen it sour people on TN altogether, which is silly because its the best. Focus on keeping solid snapshots and backups of mission critical items and your config.
Think of each jail as an independent system, the more you have the more configuration and permission issues you will encounter. Most TN users really only need one jail maybe three at most. One set of mounts, one user, one rc.conf. Keeping a jail for each software or plugin is uncle nutsy's playhouse and asking for complications. Keeping mount points straight between several jails can be maddening. K.I.S.S.
If youd like me to further what ive said here, just lmk. Good luck!
