I don't know the answers to your questions but I hope you keep monitoring the upgrade situation (thru the phone-in automated system) until you take off from IAH; I suspect your upgrade will clear later today or tonight or even Friday morning. Upgrades (at least mine) are clearing later and have been for the past couple of years.
I think the gate agents at ORD are in charge of who gets the upgrades, but someone else may know better.
Please let us know (by an update to this thread) when it does finally clear.