The earlier posts on my logging experiences didn't include the logrotation solution I used on my OS X Server.

When you create a new logfile (and have syslog fill that file up), you're gonna run into a lack of space sooner or later. This happens because the syslog server keeps writing data to that file, and the system doesn't 'recognize' (read: isn't configured) the file for logrotation. So, you need to tell the logrotation process to include the new logfile (and what to do with it).