Rob,
If the ask is to make basic auth an optimized experience again then I don't think that will happen. The Outlook Team will be deprecating it soon.
What I would like to do going forward is if there are any learnings about moving to OAuth to add them to the Known Issue article, Outlook and other apps are unable to connect to Outlook.com when using Basic authentication - Microsoft Support.
One key thing I will probably add is that when you add your account to an app, to make sure it connects with OAuth, make sure it prompts to sign in via the Outlook.com sign in dialog. If you or anyone else knows anything helpful like that please let me know and I will get it added.