After some more debugging I have determined that the database was corrupted in the update to the latest version somehow. Upon attempting to load the DB into sqlite3 it became apparent that is the case and I just simply deleted the database and re-setup the server from scratch 
. Oh well it could be worse, right?
Maybe that will also help others here is the documentation for determining and fixing a corrupted database file. https://support.plex.tv/articles/201100678-repair-a-corrupt-database
