I just got my new Blackberry 7290 and was trying to bring over my contacts/calender from Outlook express.
I installed the desktop manager and tried syncing them but it gave me an error saying "No applications configured for synchronization". So then I went into "Intellisync" and "Configure PIM" and only to see that Outlook is not in the list of items! There's Lotus, Netscape and ASCII.
You could try creating a new outlook profile. I had to do this to get desktop manager to find my outlook files. To find out how to do this look in the Microsoft knowledge base under mapi creation for outlook. You will have to backup and reimport all of your outlook days from your old profile, but that was the only thing that would work for me. Maybe that will work as a last ditch effort.