Using Classic Outlook on Windows for personal email, calendar, and contact management
This issue can be considered closed. The "missing" emails were eventually delivered, after 5-8 hours. Blame server delay, some kind of rules/arbitration, or your favorite bottleneck. I could not trace do to be a personal Outlook account connecting to M/S servers, and Advanced Logging showed no errors on the send of the test messages, or anomalies in the receipt of the limited set of messages.
So, I will have to just hope that whatever delays in the "murky middle ground" are limited and will be eventually fixed... since I have no further visibility into the serverer handling in that path of the delivery.