I sync Outlook, Blackberry and iPad using NextAction and iMExchange2
I thought I would share my experience here. For Outlook and Blackberry I purchased NextAction Pro and Desktop applications.
It's not cheap, but I think it is the best way to sync Blackberry and Outlook. I use Outlook 2007 on a company Exchange server, but it also works on Outlook 2003. The Blackberry Bold 9650 is also company on the Exchange server.
I did have Netcentrics and NextAction, but they dont seem to be compatible. So, I dropped Netcentrics.
NextAction uses Categories for Context and Projects. Each Task hence has two Categories, one for Project and one for Context. The add-in and toolbar is very reliable in creating Tasks and sorting the Task List by project or context.
One drawback of NextAction on Blackberry is setting reminders. If you create the task on BB in NextAction with your project and context, you then have to "Open in internal app" to set due dates, reminders, etc . . .
Not sure if everyone knows this, but if your company supports Outlook Web Access, you can configure the native iPad Mail, Contacts and Calendar to sync up perfectly. Use your login information and use webmail.xxx.com for the server, where xxx is usually your company www.xxx.com. Use SSL ON.
On the iPad I use iMExchange2. This app supports Outlook Tasks and Notes, which are not available on the native iPad applications. The list of Task is very nice because it can be sorted by Category and the Categories can be collapsed or expanded. One small quirk is that all the Categories are listed, so each Task appears both in the Context and the Project. I purchased the full app and it automatically syncs everyting.
One thing about configuring iMExchange2. When you enter the Server, I had to use webapp.xxx.com for the server, instead of webmail.xxx.com as I did for the Mail, Contacts and Calendar. Also for iMExchange2 I use SSL ON and Exchange 2003 ON.