Well just to report what happened, I called the Star Alliance desk and got the same message once again about the upgrades being a bit of a crapshoot.

However, she suggested we look for a business reward ticket and she found me a terrific deal on my fairly complex itinerary using miles only. She was patient and nice to talk to, and handled all my "what if we try this" questions with a great attitude. She ended the call by saying that it was "fun" (amazing!) and that she'd had a difficult day up to this point but that this call had made her day because she was able to get me the result I needed. (Until then, I'd completely spaced out on the fact that the east coast was so messed up, and it probably wasn't the best time to call.)

She also apologized that she didn't know the Star Alliance as well as she should, that she was still learning, but that she loved the new flexibility with all the great new partners. What a great attitude.^

Sometimes you get the good ones - she should be doing commercials for CO!