I'm just wondering if you have tried to do this via a 3rd Party PIM (Pocket Informant (
http://www.pocketinformant.com/) or Agenda Fusion (
http://www.agendafusion.com/)?
They are much better managers of your tasks/calendar items that Pocket Outlook (which, IMHO, is one of the worst programs ever designed) and have better ways of managing all of your functions.
Try out a demo, see if it helps, and let us know if you have any other problems.
Nick