Personally I would completely uninstall Desktop Manager and reinstall using either BES or BIS option, not Redirector. That can and probably is the issue. The fact that there is no Wireless Sync option shows that the services book don't have that setting.
I would do this:
1. Reinstall Desktop Manager with the BES or BIS option
2. Remove and readd the user to the BES and reactivate
That will eliminate Desktop Manager and should push calendar/contacts/memopad/tasks to the device. Odds are if you look in the MAGT log you will see a line that says still handled by desktop.
And Geoman....You don't have to permanently delete an item for reconciliation to work. In BES versions less than 4.1, permanent deletes are not even recognized.
For email reconciliation double check that Delete On is set to Mailbox and Handheld on the device under Messages>Options>Email Reconciliation.
Let us know how it goes.