Jumping at night over a remote area, nah. It was basically a one way mission. He either dies trying or simply faded into the wood work. Not being a jumper, I would imangine tossing one bag out, then yourself a few seconds later would be a huge area he would have to search for the money chute, possible stuck in a tree making his search a 3 dimensional trek and search at night to be gone before authorities started looking for him.
My theroy is that he jumped with the money, scattered a small amount to make it look like he died in his attempt, then made his way to a big city and lived his life out quitely above some little bar.