I don't have a Blackberry, but the phonebook uploads automatically. I might recommend downloading and applying the 2.401 update (a link is in another thread here) and see if that helps.
You speak it. Example: When I hit the uConnect phone button, I'll say something like "Call Home" or "Call so and so mobile." It will check my phone book for a matching entry, and if there is one, it will pick it out and confirm. If there are multiple numbers such as "home" or "mobile," that's why I add that to the command. If I don't say it, it will ask which number to call.
Note: the difference between "call" and "dial" seems to be that "call" indicates a phone book entry, and if you say "dial" it is expecting you to give a list of numbers for the actual phone number.
It calls for some experimentation, that's basically how I figured it out. If you have any specific questions, feel free to ask. It's easy to use, but the clearer you speak, the better it works (don't try to call somebody with a fistful of M&Ms in your mouth ). You can download the full RER manual from Jeep, and that will have some specific info on the voice commands. There's also a tutorial mode (hit the voice command button and say "tutorial," but I haven't tried it yet).