You have to move the stick around until you find the "sweet spot" which is the controller rumbling, and then hold it there. You only HAVE to use one stick, however if you use both he grabs it with two hands, find the sweet spot on each stick, and the meter drains super fast.
Try to set up the ladder as close to the case as you can.
Set up a two player ladder match title match with the second player stationary and practice on the belt.
For the Featherweights, use Giant Khali, get most of them dead and bleeding (it dosen't take long) and then THROW THEM OUT OF THE RING! They will be dead outside of the ring for AT LEAST two minutes, it gives you more than enough time to grab the case. You need to use Khali since THEIR MOVES WON'T WORK ON HIM, except for that stupid special move suplex, but you should make sure they all dead before even attempting to climb the ladder. When they are spread out not moving, all 5 of them, then you strike.
Just take the first 5 minutes to beat the shit out of the featherweights with your normal moves. In the end, I threw three of them out, gave his super brain chop to the other two (one saved special, the other earned) and by the time I grabbed the case they were still knocked out.