Lets start off with what you need to have to make this very simple, and that is a Gmail account that you are willing to put on your PlayBook. Everything else just falls into place.
With Microsoft Office, Thunderbird and other email clients, you have an option to export your address book as a CSV (comma separated value). So start off by getting your contacts exported and saved somewhere you can easily find.
Next go to your Google contacts page via the web Here once you have a Gmail account. While on your contacts page take a look at your contacts and make sure you do not have any old ones that you want removed. While on your contacts page you will see on the left hand side the menu options and you want to select the last one import contacts. When you click on import contacts a window opens up so you can browse to your CSV File you saved from your contacts export and simply select import.
Google contacts also supports importing vCard from apps like Apple Address Book.
Once you have imported I recommend going through your contacts on the Google contacts again and removing those that you may not want. If you already have this Gmail account loaded on your PlayBook, these new contacts will import when it syncs.
For your BlackBerry Device you can download Google Sync app but in all honesty it can create a mess on your BlackBerry Device with duplicate contacts because it syncs both ways. I recommend using the free DropBox for BlackBerry app that allows you to export your contacts to the cloud in a vCard format. Don’t have a DropBox account get your 2GB free by signing up here. Then download the DropBox for BlackBerry App Here. After DropBox for BlackBerry has been installed simply go to your contacts and hit the menu key and select export contacts to Dropbox.
Then go to dropbox copy and paste the vCard of your export and save it to your desktop. Then go to Google contacts and import the file.
I exported via dropbox on my device, Microsoft Outlook and Thunderbird then imported them all into my Google contacts. After the contacts finished syncing I have all showing up on my PlayBook now.
When you delete a contact via your Google contacts page or via your Contacts on your PlayBook, they will update each other.
Other ways may be available but this is how I went about it. Hope this helps some folks out.