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After some head scratching & investigation it turned out the SIS was not properly configured.
I had contacted enteo support who suggested something was possibly wrong w/ the SIS...
After running the "health report" on all of our locations many sites came up "SIS not in use"
I pinged the PC names coming up with the errors in the Analyze Client Events monitor and compared them to the locations coming up with the SIS error. What would you know a pattern finally arose.
To fix this you must manually configure the SIS. Go to the site, which comes up with the error
Lock the database --> Right Click (the site) --> Properties -->Netinstall Service (tab) --> Start Service Configuration Wizard
This will manually allow you to configure the SIS (I didn't see much on this in the books). The process is as found in the site configuration wizard.
Now, the question at hand is how the SIS got "lost". But all I know is that it is working now and the errors are dwindling after the Outbox agent finally completes the install