Thanks to everyone for your thoughtful and helpful responses. I’ve really appreciated the wisdom and advice that you all shared.
As of 8 pm tonight, #2 is far ahead of #1 (this may change by the morning, but hopefully not!)
And there’s now an option #3 - not apply ED to either #1 or #2 and instead send his app to an REA school that’s a huge reach but could be a great option. He knows this is most likely (but not 100%) giving up the possibility of #1 but he’s okay with that since he does prefer #2.
It’s going to be a long weekend writing supplements!