Hammer and Rage are right. The best way to do it is with a particle instancer. You can randomize attributes like the speed, lifespan, size, etc that way. Then you can use a ramp or an equation to fade out each particle and use the particle sampler node in the hypershade to transfer that data to your shader so each dollar sign will fade out independently.

The thing is, it sounds like all if this is a bit beyond your skill set. (I apologize if I am mistaken). The simplest solution for you may be to animation each object by hand, duplicate your shader for each object, and then animate the transparency for each shader.

Either way, good luck.