Using the New Outlook for Mac features in business environments
This problem persists in Version 16.110.1 (26062112). I believe that it relates to the way that Outlook is now building the HTML that underpins the message.
I can see within the HTML of a (broken) message sent from this version on the Mac, that we have the following...
<div style="direction: ltr; font-family: Aptos, Arial, Helvetica, sans-serif; font-size: 12pt; color: rgb(0, 0, 0);">This <span style="font-family: "&quot;Courier New&quot;", Arial, Helvetica, sans-serif;">should</span> be courier</div>
Notice how the inline <span> has a font-family defined, but that the attempt to put quotes around the selected font name has produced an absolute mess.
The equivalent in an email sent from a Windows machine looks like...
<p class="MsoNormal">This <span style="font-family:"Courier New"">should</span> be courier<o:p></o:p></p>
Interestingly, if I view the source on the Windows machine, I see...
<p class=MsoNormal>This <span style='font-family:"Courier New"'>should</span> be courier<o:p></o:p></p>
So there is a double problem with Outlook on Mac converting single quotes to doubles in received messages, and then mashing inline double quotes into ", in addition to whatever the heck it's doing when composing messages. If someone wants to pass that on to anyone that can actually fix this mess, then please do so.