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Hello Mark,
Let's figure out where those emails went because a standard OS update normally won't wipe your mail out of thin air if it is synced to the cloud. I just have a few quick questions to diagnose this properly.
What kind of email account do you have linked to Outlook? I need to know if it is a Microsoft account like Outlook.com or Exchange, or if you are using POP or IMAP from another provider.
Also look at the top right of your Outlook window or in the Outlook menu at the top of your screen. Do you see a toggle or checkmark for New Outlook and is it turned on right now? The app sometimes switches over to the new version automatically and that version temporarily hides any local folders saved directly on your computer.
Lastly did you just run the standard upgrade through your Mac system settings or did you do a completely clean install wiping the hard drive for the new Golden Gate OS?
Let me know those details and we will go from there to get your stuff back.