Now that I think about it the shape/type of the headphone shouldn't matter, what should matters is the frequency response that reaches the eardrum, it shouldn't matter how it gets there. If the architecture of a headphone affects the ear resonances (for example an iem bypassing the outer ear resonances), it should compensate for it with it's sound.
I got this message from headroom in response to a question a few days ago:
"The frequency curve compensation is the same for in-ears as well as full size headphones. Yes, you can compare them side by side. However in a real world application, there are things like noise isolation and soundstage that affect your experience that measurements can't represent properly. The measurements are a great tool as a guideline, but they don't represent 100% exactly what a headphone sounds like. Just keep this in mind and please let me know if you have any other questions."
Here Tyll explains his measuring procedure - the compensation he uses is an HRTF, and is independent on the headphone:
http://www.innerfidelity.com/content/headphone-measurement-proceedures-frequency-response
Still, it's quite hard for me to find a headphone and an iem that measure similarly and are considered to find the same, just as the fidelio guy pointed out (although i didn't look very hard). maybe someone else can help with this?
@bigshot we make it complicated because its fun and makes us feel scientific ^^ though hopefully it's simpler that we make it to be.