First, let me thank everyone for jumping in. Great discussion.
I saw a few questions and comments that I want to try and answer. I will try not to miss any.
First question.... Did I match by ear or SPL? By ear, and I can tell you that it was a long day of auditioning so my ears were getting pretty fatigued so I certainly could have been off.
An additional Note .... I went ahead and installed "Boom" on my Macbook Air. Mostly because of the ability to EQ vs. pushing more signal through the port. Boom has two settings, one for straight up amplification, and the other for EQ, they can be set independently. It does mention a "cleaner" sound on the web site but I could not find anything about how it was cleaned up so i figured it was just marketing.
The result ...
1) With Boom Off... flat sound, good but not exciting... had to push the power almost to the edge to get something to come alive and even then stayed a little flat even though it ware really loud at that point....
2) With the Amplification Turned on (and then volume turned down to match SPL) ... Much more alive better response and clearer sound all around even at what seemed like lower output SPLs then before... Again balanced with Ears.... All around very happy with the sound the....
3) Finally turned the EQ on pulled up the low and high into a subtle V and really got to "My sound". Loved the 940s bass very clean and tight and went much lower than I remember. The highs clear and tight too (see below) Note that that last step was fun, but not necessary to get what I thought was very alive sound. I literally had to go back and forth several times to see if I really liked the EQ on or off. But definitely needed the "amplification" on to get the phones to come alive.
Second .... I would not be at all surprised if the Mryrad put a bit of a curve on the sound to liven up the 940s. That was actually part of my original question (thought I might not have said it well). An interesting question would be if that is the case would the Schiit Vali but a fun thing to test as the Tubes should be a bit of a Warmer sound (never tried tubes but that is what I hear). The amp drives quad 22L speakers, I often wonder if this setup is a bit too warm.
Third ... I never really had a problem with the volume level on the 5s (at least not for my 940s) they just did not seem to have that umph. Loud but not clean (see below)
Last ... One thing that I definitely seem to notice (but am willing to consider that I just convince myself of) is that amplified the 940s seem to bet much crisper. One of my test tracks is Florence and the Machine - No light, at around 1:35 - 1:55 there is a section with a harp, some background strings, heavy drums, the whole 9 yards. Unamped (and in many of the headphones at the lower end of my list), the harp notes are there, but you can't hear the "pluck" of the strings, the strings come on, but they are not clear, and the drums overpower the voice (guessing that for a Florence song, the voice is definitely what should be highlighted), background vocals which are a much lower registry than Florence almost disappear completely. BUT when amped, even with Boom and no EQ, you hear everything, the drums are clear but at the right level, the notes on the harps are crips, the string section is much more fluid and the voice comes out to the front. I don't see how that could be caused by a EQ curve as the effect is that all areas of the spectrum are equally clearer. I would expect a EQ curve to bring the emphasized area forward (and it does when I but the BOOM EQ on), but it seems to get cleaner across the entire spectrum not just where I push up the gain in the EQ. Thoughts???
Thanks again. This is hugely helpful.