What version of Microsoft Office are you using?  I had trouble syncing with my laptop and as it turns out the newer versions of BB Desktop Manager won't recognize Outlook 2000.  You need to purchase/load a newer version of Outlook.  Don't know if that is the issue, just a thought.   Fortunately I had Office 2009 that I bought for my desktop.  Once I loaded it on the laptop it synced without an issue.  I prefer the older version of Office, but you have do what you have to do.