Persistence. I found the magic combination:
Authentication: Shared
Encryption: WPAPSK
Radio: A
Pass phrase: My Exact Password Is Entered Here
Network Key: 256-bit
Network Key Value 0: The Derived Key [Used JavaScript PBKDF2(password, ssid, 4096, 256) to generate this.]
Network Key Value 1: blank
ReKey Internal: blank
SSID: My Exact SSID Is Entered Here
Guessing it was the lack of Network Key Value 0 the whole time. Off to the races! Hopefully this will help someone else.