Re: question 1, I updated my MP account info recently and received the below email within a few minutes of signing out of United.com. Fwiw, to the extent you have his MP#, record locator, birthdate, etc., you might also want to consider just calling United and seeing if they will allow you to just purchase the upgrade for him over the phone without taking over his account. (Policies may have changed, but I was successful doing this this a number of years ago to upgrade a friend flying home for her mom's funeral. Could be worth a shot). But I'm guessing whichever path you take, he's going to wind up getting at least one email, either notifiying him that the account info was updated, or notifying him of an update/confirmation of his upcoming itinerary. If it were me, I would be prepared with a good story about how you had credit card points/flight credit/something else that was going to expire and would go to waste if it weren't spent on this upgrade. Good luck, I'm sure they will appreciate it in the end!