Update: After 4 hours of poking and prodding the settings to no avail, I finally just went to:
Geodirectory >> Uninstall Settings and checked “Remove all data when deleted” for both GeoDirectory & GeoDirectory Events.
Had to basically start over from scratch but at least it’s working now.
TL;DR Even a blind squirrel finds a corn every once and awhile. Only when it’s off the cob though.