Using older versions of Outlook for Mac for personal email and calendar
Sorry for the repeated posts, but unfortunately after letting the Outlook reindexing run all night, the search feature still didn't work. I ended up calling Apple for help and because search wasn't working on Apple Mail either, they were willing to work with me. It ended up requiring me to re-index my entire hard drive, which we did by adding the hard drive into Spotlight/Privacy and then deleting it again. Within 90 min, the search feature in Outlook was working again (but ironically, the search in Mail still didn't work properly). In case it helps anyone else...