@timo - Thanks for the suggestions. The steps you suggested above, didn't resolve the issue, so I took a few extra steps that seemed to work. The extra steps: 1. My wife logged in/ out as described above 2. My Wife also went to account settings and scrolled to the bottom to "reset the purchase warnings". 3. I did the same 2 steps shown above. 4. I ALSO went to the payment screen and swapped our secondary card with our primary card (you can re-arrange the payment priority). Not sure if step 3 or 4 made the difference but altogether this seemed to work. (A quick note, my initial payment was set to Card (credit card)... but I transitioned a different credit card into the primary spot.)
Bottom line - we are back in business and my wife was able to purchase an upgrade to Pro.