If you pulled on the bottom of a multiple pulley while an object was hanging from the end of the multiple pulley’s rope, would that object feel heavier than it really is?
Yes. If there were 5 segments in the multiple pulley, then you would have to pull down on the bottom of the multiple pulley with a force that was 5 times the magnitude of the object’s weight in order to lift the object at constant velocity. But the object would also rise 5 times as fast as the end of the multiple pulley would descend.