After getting frustrated, here's what I did eventually to find that there was a very simple fix. Grrrrrrrrrrrr...
1. Reinstalled entire PDA
2. Reinstalled WMDC
3. I repaired Outlook and did a scanPst (C:\Program Files\Common Files\System\MSMAPI\1033
Nothing solved the problem, finally this is what did it.
http://www.microsoft.com/windowsmobile/devicecenter//troubleshooting.mspx
- Windows Mobile Device Center fails to connect due to the Windows Portable Device driver failing to load. In some cases, you may be unable to connect and only a red X error icon is displayed in Windows Mobile Device Center. This can be caused by Windows Portable Device driver failing to load.
- Connect your device
- Go to Manager (Computer > Properties)
- Find the Portable Devices node
- Locate the Windows Mobile device entry
- Choose to uninstall the driver
- Reconnect your device
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