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Okay, so I finally got it working but it was more of giving the whole process a 'kick' that may have got it working.
Short version:
Adding the phone that worked immediately after adding the failed phone while still leaving the failed phone in the 'failed CarPlay' state seemed to get things working for both phones.
The long version:
I had reset network settings on the iPhone X that was having issues. This effectively removed all network connections and renamed the phone to iPhone. I removed all Bluetooth connections from both the car and that phone. I also removed the working iPhone 11 Pro from the X5.
Adding the iPhone X resulted in the same errant behavior. A few additional reset and restarts of the iPhone and X5 didn't change anything. At this point I was about to give up but wanted to see if the iPhone 11 Pro would join the car and connect through CarPlay again. I left the iPhone X in the state where it only showed the CarPlay icon but not connect (worked fine for Bluetooth calls with iDrive but not CarPlay).
With both phones next to me I started to add the iPhone 11 Pro and I was prompted by a message on the iPhone 11 Pro asking if I wanted to use CarPlay and at that same time the message also popped up on the iPhone X which was sitting 'ON' and on the seat next to me. This message never showed up on the iPhone X before. After acknowledging the message, both phones where paired and worked with CarPlay on the X5!
I've never run into this problem with two other BMW's so this is a bit strange for me. I still think something wasn't (isn't?) right with my wife's phone and it seems to have failed on her phone at the state of pairing when there is a handoff between bluetooth over to Wifi for CarPlay to work.
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