It looks like monit is working fine, but it's either not finding the pidfile in the right place or transmission is legitimately not starting correctly. Then, when it tries to restart the service, there's an error with the rc task.
How do you have transmission configured? Have you been starting it via rc? Is it enabled in /etc/rc.conf? Where is transmission writing it's pidfile?
Transmission configuration:
I followed this guide exactly:
https://www.reddit.com/r/freenas/comments/41fhz3/configuration_guide_for_openvpn_and_ipfw_so_that/
I haven't been doing anything different from the above guide to start it. Just reboot and it's there.
I think it is enabled in rc.conf by default when installed through the plugin GUI. But, am not sure?
I don't know where the pidfile is. It would be the default location that the plugin GUI sets up.
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I get the impression that monit is running. The errors at start-up, I think, are because its still booting up and the startup delay isn't long enough? Maybe I am mistaken about this.
It seems like monit is running because it does restart transmission. It just does so very frequently. Every few minutes.
And unfortunately, even with the frequent restarts, it still gets complete frozen like before and requires a manual jail reboot to get everything working again.