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After some more digging I found the following error:
20090302140322 I #864 Script CheckSiteStatus:<my server> is not upto-date site. PolicyCatalogVersion=20090302184254, RepositoryCatalogVersion=20090301171611
What does that mean? This repository has the same version of DAT's as the master ePO server.
Fixed: I think.
My master repository updated its DAT file while I was doing my testing and made my local repository out of date. I forced a replication and now it updated fine. So it looks like the hosts that are repositories check to see if they're up to date before they update. Weird. :confused:
I have my schedules set now so tomorrow should go smooth. silly