Here's my setup
Work PC:
Outlook with GTD plug-in
Sync to Windows Mobile handheld
Home Mac:
Missing Sync for handheld to iCal
OF-iCal sync
-Tasks created in Outlook have the category set the same as the context. The contexts come into iCal as separate calendars.
-Tasks created in OF sync to the corresponding iCal calendar
Work PC:
Outlook with GTD plug-in
Sync to Windows Mobile handheld
Home Mac:
Missing Sync for handheld to iCal
OF-iCal sync
-Tasks created in Outlook have the category set the same as the context. The contexts come into iCal as separate calendars.
-Tasks created in OF sync to the corresponding iCal calendar