You should evaluate Companion Link http://www.companionlink.com/downloads/index.html . They have a 14 day trial and you will be amazed on how good it works. I have used it for about a month with no problems. I have some other technical issues with ACT2008/Outlook 2003. But I do not feel they are related to this program.
FYI ...Companion link has been around for a long time. The first version allowed Act notes to syc with Palm Pilots.
DoubleLook, which I just completed evaluating, is one of the CompanionLink products. DoubleLook worked ok; a few issues; no bells and whistles; and I believe a little costly for the limited functionality.
To sync with Outlook, you need to use DoubleLook from www.CompanionLink.com - you can download a trial and test it. If you decide to order, use the code GL6766 to knock a few dollars off the price.
But, as Outlook doesn't support all the fields and information in ACT!, you won't get all your data. Also, as Outlook doesn't link activities to contacts, new activities you create will all be associated with your My Record.
If you don't really need Outlook, but just want all the data on the Blackberry, the best solution is Handheld Contact - go to the link and you can set up a 14 day trial