So my solution...patience. I had a 17gig Outlook file, I let it load/sync overnight however that was not long enough. You need to let your files completely sync prior to expecting the Outlook to function properly. It works fine now. The Progress Status under tools led me down the correct path and let me see the issue. I am running my PC at work, my Mac in meetings / home / on the road and another PC at home and iPhone all connected to the exchange server and operating correctly.
Technical Canned Answer:
You can Control-Click (Right-click) on a folder and select synchronize now. The number of messages in your folders might need to be reduced to match what works on a Mac. If you do have large numbers of messages to move, I would do this in your web browser then create a new Identity in Outlook Mac and let the changes download to the new Identity.
Be sure you have updated to 14.2.2 first!! The SP2 updater had a major database upgrade.
The Inbox syncs more frequently than any other and should be kept as clean as possible. (this is the number one cause of problems with sync). Do NOT make subfolders under the Inbox.
Any folder with more than a few thousand messages is going to take some time to fully come down when you first sync your account. Due to the design of Outlook's sync engine (and how exchange works), you will see the 512 newest messages in a folder at the initial start of sync then the rest of the folder's contents will be back filled before you see any mail that arrives after this point. This is why it will look like you are not getting new mail when a folder is still going through initial sync. This is also further exacerbated by an Exchange issue where it gets unnecessary change events before the newer mail arrives. If you carefully watch the progress during the sync of a folder with greater than a couple thousand messages, you will see "Updating local..." a lot before the newer mail starts arriving (newer than the initial 512 that come down).
Outlook checks the server for updates every minute, any folder that has updates will subsequently be synced. Since Outlook has a limit on how many folders can be synced at a time, there can be a queue of folders waiting. The Inbox does get high priority so it will generally sync before other folders that also need to sync.
Recommended Mailbox Size Limits