I have had Outlook 2000 working with a Blackberry Curve and the Desktop
Manager but RIM doesn't even support the desktop redirection software. Check
the carrier website (Verizon, Telus, Rogers, whoever) for any patches to the
Desktop Manager and you can even call them for technical support. They're
usually quite helpful and their website should have a good technical FAQ.
The Desktop Redirector is flakey at best but they do offer some nifty
troubleshooting tips for you. I ended up switching to a BES once we had
enough users to justify it so it's been a couple of years since I had to deal
with the Desktop software.