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Your question 'is MIDI actually a HID device' took me by surprise. I searched the web for more information to make sure that i use the proper terminology (Midi , USBMidi, HIDMidi, Midi over USB, etc.) and among others i found this interesting post by Paul Stoffregen.
http://forums.adafruit.com/viewtopic.php?f=51&t=51683&p=262051#p262017
You might know more about this than me then - is MIDI actually a HID device? It looks a lot like it's a special (non-HID) device type.
While actually letting people specify custom descriptors isn't that difficult, I think realistically it's not going to be very useful. I think you'd need far more than a passing knowledge of USB to do anything with it...