The problem now was that after the calendar appeared to be completely downloaded, it would disappear and download itself again. As if the user had selected to "Empty Cache", but the user didn't do this. This would occur over and over again, making delegate access useless since you don't know where events are to schedule new ones in open spaces.
The fix I applied was to delete a sub-calendar in the primary user's calendar and also to run the OutlookTools 2.0 utility on the primary mail/calendar account on a Windows XP machine. (Note, this is NOT on the Mac/Entourage delegate system.) The problem appears to be caused from the account itself and has nothing to do with the Mac, or Entourage.
The small tool can be downloaded from http://www.howto-outlook.com/products/outlooktools.htm , below I show the switches I used. Before using this tool I manually ran the switches below and this did NOT correct the issue.
"C:\Program Files\Microsoft Office\Office11\Outlook.exe " /switch
/cleanfreebusy
/cleanreminders
/cleanschedplus
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