Lets eliminated two false concepts first. No the earth can not wobbly under a stationary pin to make a mass that is unwinding from, or wrapping around the pin to make it go faster or slower. The Newtonian linear momentum of the mass remains the same. No there is not a huge amount of friction when a wrapping mass winds up or unwraps from the pin. An Atwood's or modified Atwood's makes far more momentum than the same distance of free fall for the extra mass. You can place that extra (all that) momentum into the same extra mass and it will rise 10, 20, 40 times higher than the distance it was dropped. The height increase depends upon the mass ratios used. The momentum of the Atwood's can be placed into the small extra mass by the 'cylinder and spheres'; which can be found on YouTube.