Is there a way to tell this from measurements? or measure the degree of openness?Headphones have degrees of openess and closedness
If an electrostatic headphone, a planar and a dynamic headphone are all eqed to have the same bass will they all sound equally 'dynamic' is there a way to measure this?They also may have different dynamics and handle bass differently
Are there any measurements that help one judge how transparent a DAC or a headphone is?An oversampling DAC should be able to give you transparent sound within the audible range.
I am not disagreeing with anything you said, the science to judge these objectively may already exist, it is not something that is researched enough and published. The alternate possibility is it is all audiophile myths, they should all sound the same.