This is on my to-do list, nice to have but keeps dropping to the bottom of the list.
Some thoughts :
Cronify seems to be an option, at $99 pm for 100 users it could make sense if you on-sell the feature to mitigate the costs.
Alternatively , Sync2 seems to be a cheaper option, if your customer user is prepared to pay $49.00 once of lifetime license. With this option, you would have to set up an FTP server to facilitate the syncing, and then have your Aware app mirror the syncing on the server-side. https://www.sync2.com/sync2-features
Alternatively 2, by having a button on your calendar to update Outlook, when clicked a download of the appointment data as a file formatted as an ical layout (.ics) This will automatically open in Outlook , if set up correctly on the user side, requires user to save though. Very basic as its only a one way , unless you get creative and embed a link in the ical file (update AIM) that can be clicked on to login to Aim to update appointment