Just to try, I would uninstall re-install the BlackBerry Desktop Manager but I would try Version 4.3 or maybe even 4.2.2 but I would try version 4.3 first.
You can also run a scanPST on your PST file although since you haven't had any previous problems with Outlook that might not help too much.
Have you tried sync'ing the BlackBerry on another computer or no?
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8830 -> 8330 -> 9550 -> 9650
Just think about how far BlackBerries have come from then till now... And what else is coming.
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