1) My calendar is not syncing on the phone with what I have at work, I must be missing something!
If your BES is on the same box as the Exchange Server then the Calendar is most likely due to permissions. What account did you install the BES as? Any admin accounts break the Calendar. Use this article to create and switch your BES to run as the BESAdmin:
BlackBerry Search Results
If you create an appointment in Outlook will it sync to the BB? Calendar should sync in one direction. If not check to see if wireless sync is enabled on one of the devices Calendar options.
2) My personal contact have sync'd but the Global Address Book did not, is it supposed to?
No, the GAL is only for Lookups.