Howdy again markanini.
I have used and tried a number of different approaches to EQ-ing. And continue to experiment with new ideas along these lines. I'm not sure that I've used an iterative approach exactly like what you describe here. I have used an approach where I listen to and EQ a number of different songs though. And then compute an average EQ curve for my headphones based on those. The table posted here was one example of this...
https://www.head-fi.org/threads/bey...pressions-thread.702948/page-31#post-16046298
What I've been trying to do lately though is figure out an easy way of combining the sound signatures of multiple
headphones together. Perhaps using kind of an iterative approach somewhat akin to what you describe here. I believe there is an an app that can already do something like this. Which allows you to EQ your headphones to sound like other headphones. And also to combine the responses of several different headphones together, which is pretty cool.
The simplest way to do something like this would probably be with a spreadsheet. I think I've figured out a temporary work around that I can use in Equalizer APO's Configuration Editor though, using it's stacking feature, to potentially save me some of the rather heavy-duty number crunching that's involved with this. (I may try this approach for computing the average sound power for different sets of loudspeakers as well!)
If I stack all the EQ or headphones response curves together in the same project, the Configuration Editor's Analysis Panel will basically show me the combined result of them all added together. At that point it should be fairly simple to compute the average by simply dividing (or scaling) the final result by the number of EQ or headphone graphs in the stack. There are a couple other steps involved. But that's the basic idea.
This should hopefully allow me to try more combinations of EQ, or response curves without having to manually add up the values for all the points, as I've been doin up to now. Which is one of the things which has been slowing down alot of my graphing lately.