Kali Linux on Headless RPI4

Last week I flashed Offensive Security's latest release of Kali Linux (2020.3) for Raspberry PI 4 and have spent probably close to 10 hours now trying to get it to connect to my 2.4G wireless network to no avail. I can get it to connect after login (when I login using my screen and keyboard), and can get it to join over ethernet (without logging in), but for the life of me, I cannot get it to connect over 2.4G wifi on bootup using the typical method of placing the empty SSH file and wpa_supplicant file in the /boot directory that is demonstrated on all the popular forums (e.g. Null Byte's CyberWeaponsLab).

What makes this especially frustrating is the fact that there are no error messages to provide any clues. It simply does not show up on a network scan until I log in.