Actually the way I would do it which really is not much different but might be beneficial with his higher status.
He makes two - two night reservations and he also either makes a one night reservation for two rooms or two one night reservations.
You then call in and have them take the points from your account for whatever combination of the 50k you desire and exchange his cert for yours.
If he doesnt have enough points to make all the initial bookings then conference call it.
The above will make sure his gold status goes with both rooms for the three days.
Stayed at that property in Feb, its fine.
mike.