HowTo: Sync Contacts from Outlook to Playbook
Warning: I am just sharing the painless way I accomplished this task. It may not work for you as it totally depends on your email provider if this is going to work or not.
I use Outlook and pop3 email accounts provided by my ISP. First thing you need to do is log on to the webmail server usually provided on the hosts website. Look around for something that says "Import/Export", mine was found under the "Preferences" section. I had the option of importing .csv files from outlook for contacts and calendar. If you can't find it, or they don't provide that feature then unfortunately your journey ends here.
//edit It appears google also has the Import/Export feature! So you should be able to use your gmail account to accomplish this.
Next, go into Outlook and select the "Contacts" tab at the bottom left. Next go to File --> Import and Export --> Export to a File --> Comma Separated Values (DOS) --> Select "Contacts" in the folder tree --> Choose a location and SAVE.
Back in my webmail in the import/export section, I just browsed for that .csv file outlook created, uploaded...and boom. All my contacts on the playbook. Of course the email account you are choosing to upload the .csv file to must be registered with the playbook. The calendar can be sent to the playbook the same way. No need for any google software or giving a 3rd party program access to your gmail account.
Again I realize this might not work for everyone but if it helps a few people then I'm glad :)
I got this to work for me
This worked for me. I use bell as me service provider (internet) @sympatico.ca email
using windows vista, windows native email program
Click contacts->click export->highlight CSV and click export->choose a name for the file and destination where you want to save the file (documents,desktop etc.)
exported .csv file to my desktop
Logged onto my @sympatico.ca web email account and imported the .csv file
confirm the .csv file imported to @sympatico.ca
Log out of @sympatico.ca
On playbook, touch 'add new account->email,calander and contacts->advanced setup->hotmail
Enter you info
**username and email address must be your @sympatico.ca email
**password must be your @sympatico.ca webmail logon password
continue
make sure all the sync items are set to on
save info
exit settings
if your contacts don't show up right away, go back into settings, touch the edit pencil icon, select the sympatico email, calendar,contacts account, make sure all sync items are set to on and click save.
This worked for me. good luck!