I was able to also reliably get my program to a state where the WiFi would only successfully connect on every other try.

On success, it would print: wifi:state: assoc -> run (0x10)

I knew it would fail when it printed: wifi:state: assoc -> init (0x2c0)

After I used idf.py to disable WiFi NVS flash (KCONFIG Name: ESP_WIFI_NVS_ENABLED), I was able to reconnect every time successfully.