Gabe_Bratton I matched Travis so I know I'm not a new dataset, but my search is working now as well. I had to close and reopen Outlook about 8 times and also restarted my workstation once.
Also, I did something that may have muddled my results. In the File->Office Account section of Outlook it has always shows mailto:bbaker@domain.onmicrosoft.com on the left beneath the Microsoft logo/"Subscription Product" section. To the left of that under "User Information" it has show my specific Active Directory user account which has a different subdomain than my primary email address and does not have a Microsoft account associated with it in any way (mailto:bbaker@domain-xx.int). On a whim, I clicked "Switch Account" and was presented with three options; mailto:bbaker@domain.onmicrosoft.com, mailto:bbaker@domain.com, and mailto:bbaker@domain-xx.int (A/D Account). I switched it to the @domain.onmicrosoft.com account, closed Outlook, reopened, and THIS was the first time search worked for me. Search now continues to work regardless of which of those three accounts I set and after multiple closes and reopens. I do not know whether this actually had ANY effect or whether it was just that magical 8th open/close that got things working.