replace the HD 800's with any "high end" headphone. Basically is a expensive setup that includes the CDM worth the money if the music is not HIFI?
I'm not sure what you meant about replacing the HD 800's, but I have an answer to your other question. Whether or not any upgrade in audio equipment would benefit if the music is not if hi-fi would be an entirely subjective answer that would vary vastly for each individual, as well as, IMO, would be mainly influenced by the mastering quality of the source music and the bit-rate / codec it's encoded to.
I would say that MP3s have the potential to sound 1/3rd as good as WAV at best, being their highest bitrate is 320k; while AAC seem to sound as decent yet at a slightly lower bitrate. OGG I would say is 2nd best to WAV at its' maximum encoding of around 400-600k (variable bitrate), while FLAC and WAV sound comparible, especially at the "0" encoding which is FLAC's least compressed conversion level. There are even better formats than WAV (which is CD quality of 1411k), such as DSD, AKA SACD format.
However, the underlying aspect of all music quality is the mastering; in which the audio engineer (if there is one) makes the music in a way that utilizes a broad spectrum of frequencies in a lifelike way and uses compression / stereo imaging, levels, reverb, etc. properly. If this is done poorly then it can actually sound better or a crappy system because hi-end gear often reveals these flaws so an audio equipment upgrade is pointless; whereas a well recorded song may have fine details that can only be heard on a hi-end system yet not noticeable at all on a crappy system.
So I would say, as long as your music is mastered half good and is at least 256k AAC format, an upgrade in DAC / AMP / headphones would still make your music shine noticeably better! For me, when I tried out the CDM, I was forever in awe of its' unlikely pairing with Chinese budget audiophile headphones called SoundMagic HP 100. It made these sub $300-ish headphones shine in a way I've never heard them before with a 3D soundstage that was like stepping into the middle of a new reality, full of lush vivid textures across the entire spectrum. But that's not to say another headphone can also pair as handsomely with the CDM as well.
... not to mention the HP 100 sounded this good just out of the SE output, and it's also a closed headphone.