It downloaded some (current month - May), then I had to hit the Sync Folders button to get it to sync more, then it would only sync a few at a time, facing me to manually hit the Sync Folders button again, and again, and again. However, when I did this, Outlook did not (would not) download all the emails in my existing Inbox.
When I installed the new version of Outlook that supported the NEW Google connectivity, I had to delete by old account and create a new one, which I did. It took some time (4-5 hours), but it downloaded all of them in one process. When I set up the connection, it immediately started downloading all my emails from my Gmail account. I had an IMAP Gmail account connection set up that worked perfectly. I wanted to use this new feature (new Google support) in Outlook on my Mac.