Dear Joe Chapman
Good morning! Thank you for publishing in Microsoft Community. We are happy to help you!
Based on your description, I have a general understanding of your problem, and also done some research and testing, about the search function in Outlook for Mac, please kindly refer to the following official document for more details, thank you.
In the meantime, regarding what you said, it is true, because Outlook for Windows and Outlook for Mav belong to two systems, and their functions cannot be synchronized, so if you think there are some areas that need improvement, then we are very sorry for the trouble and inconvenience caused to your work! We understand your feelings, but unfortunately, our forum does not have permission to help you change, because the feature of the product are decided by the development team and the design team of the product. And about your suggestions, I also believe that this is the voice of many users, everyone is anxiously looking forward to early improvement, in order not to waste more time and better help you, I strongly recommend that you submit your valuable suggestions to outlook feedback so that relevant technical developers and designers can see your valuable suggestions. Please believe that the relevant departments of Microsoft will strive to improve themselves after seeing your valuable suggestions, and your valuable opinions will also help more users and make the work more efficient. Thank you in advance for your contribution!
About how to give feedback to outlook, please kindly refer to How do I give feedback on Microsoft 365? - Microsoft Support
In the meantime, you can also use this link to see if the feature you want to implement is already being developed by Microsoft, please also kindly click on it to get the development progress: Microsoft 365 roadmap
Thank you in advance for your understanding! Your patience and cooperation will be greatly appreciated. I hope all the best!
Sincerely
Kerry Chen | Microsoft Community Moderator