I try to familiarize myself with the Circular Pocket Wizard

What is the Ramp Distance?

How you define CW & CCW (looking from the top down or ?)

Why they are two setting for CW & CCW ? One on top of the bit icon and one for the spindle direction. I mean if the spindle is set to CW wouldnt the bit also turn CW?

Not looked at the wizard for a long time but to answer your CW/CCW questions, one is spindle direction and the other is the direction the toolpath will go.
Hood