Well, we got the Headphone Harman Curve to rely on as a Target Curve....which is kinda all we got when it comes to measurments & targets. That doesn't show a peak at 7kHz, therefore if you're EQ'ing to the target curve then you'd remove that peak if it was consistent across all your measurements. I can't really speculate on the finer points you make. More specifically re your measurements, I'm not sure you can really use them to EQ your headphone, because it's not like you'd overlay the Headphone Harman Curve on your measurements and then EQ to that, because the Headphone Harman Target Curve is only specific to that particular GRAS unit and not your own head & HRTF....so that's not valid. If you've got in ear microphones (which you do), then you could have a stab at creating your own Target Curve......I've loosely thought about doing that in my own room with my flat anechoic EQ'd speakers which are at equidistant triangle from my listening position....do a REW sweep & measure from those in ear microphones, that would be a simulation target of your speakers in your room.....don't know too much about the specifics of making this happen as not researched it due to not really needing to as Harman Headphone Target sounds accurate to me. Could be an interesting project, sure people have done it before. You'd then measure your headphones on your head like you have done, and then EQ to your determined Target Curve. I'm certain there's lots of practical pitfall details associated with trying to do this!
Well, the latest version of Earful actually has a feature designed to help equalize headphones to speakers. It alternates the test tones (or noise bursts) between speakers and headphones, with speaker level kept constant while headphones being adjustable along a frequency spectrum. You decide how much of the frequency range you want to cover, and with how many data points. YMMV