I was finally able to work around this and get it working.
I used "IP Scanner" app on my MacBook to scan my network and find the IP address of the Obi100.
Once I had the IP address, then I could log into the ObiTalk device and upload the latest firmware.
Form there then the configuration went flawlessly.
Moral of story: If you are getting errors that indicate firmware update is required, find the IP address through a different network tool, then you can proceed with setup after the firmware is updated.