This node has 3 jobs that are nearly identical...and are the only ones we have that are deployed to the MSDB store...so compare the sysjobstep's command for each and noticed a difference:

The 32-bit run-time was enabled for this (which I thought we had set back on the SQL 2008 EE version prior to this server's 2014 EE build)

I reran the job, and it was successful...

Weird.  So when I go to the actual node via RDP and attempt to open SSMS 2014, I still get the error about the evaluation edition being expired...yet all services appear to be running just fine.

Is it possible that someone pulled a bonehead move and initially installed a trial version of SSMS only, and then reinstalled the enterprise version on top of it?  If so, why would it break after 305 days and not 180...and why would only that 1 job be affected...???

Seems to be like something changed on the actual server at the OS-level...an update, etc.