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bbfa235
(Get the code!)
After more digging I realized the Remote wasn't on the same checkbox-ng version the Local was on. Had a PPA issue that needed to be corrected. Once the Remote was successfully updated this issue went away.
That said, tracebacks like this should be handled better and the error output should be more useful.
On the remote I had version 1.0.0 and on the Local I had version 1.1.0, hence the issue. Both are now on 1.1.0 and working fine.