That much HAS been done correctly, definitely - and it doesn't work......?
With all of the issues you've been having, and with even the basic "tail" utility not working, I'm not 100% certain your jail is healthy. The latest update requires bash, and it very well could be that you may have bash installed, but it isn't working correctly.
Liek Nick said, I'd take a long and hard look through crashplan logs for any clues - spend some good quality time and dredge through the logs. The logs are, indeed, extremely detailed.
At this point, I'd also start seriously considering a nuke and rebuild, especially if this jail has been around a long time. At the every least, you'll be starting from known environment, and you should be able to just go back through this thread and follow the steps that were outlined. A newly created jail won't have ancient versions of pkg that needed to be force-updated, for example, along with any other old cruft that may have broken during a borked subsequent update.
P.S. - I don't bother setting up SSH in the jail itself - there's no real good reason. I do have SSH set up with a keyfile and a password for the main FreeNAS install, then just use jexec if I need to execute commands within a jail, or you can browse the file contents straight from the main account. For example, if I have my Crashplan jail in a dataset called "Jails", and my volume "MainVol", then you can just got to /mnt/MainVol/Jails/Crashplan" to get to the root folder of your jail.
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