Using older versions of Outlook for Mac for personal email and calendar
My solution is still working -- no emoji problem anymore. Here is what I did again: I am not sure why, but switching from the old Outlook format to "New Outlook (in the top bar), then composing a message with an emoji and sending it did seem to work. The wheel spun in the new look for a bit. But then I went back to the old Outlook format and tested sending an emoji and all worked without a delay. Strange, but effective.