I like the idea!
One issue with this comes to mind:
the ear canal is not straight, it is bent. On many individuals there is no direct line-of-sight from the eardrum. See example of a real-life ear canal below. (the eardrum is to the bottom-left, the ear canal entrance is to the top-right) The position and angle of the first and second bend is not identical for every person, and in many cases will be shaped such that a straight line from the eardrum to the canal entrance is not possible. The direct consequence is that we can not always look at the eardrum from the outside and hence also not point a laser to it. Meaning we would need to insert the laser emitter into the ear canal, obstructing it. An obstructed ear canal obviously affects the acoustics
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We do have probe microphones that can be inserted into the ear canal, but those have a limited frequency range - because we can not insert them directly next to the eardrum. Audiologists regularly use those when fitting hearing aids, but they only insert them about 3mm away from the eardrum, limiting the accuracy to about 8 kHz (which is all that audiologists are interested in anyway, that's all that is needed for hearing hearing aids).
What do I even say other than: Please read the actual research results. This is not what happened.
I don't generally recommend using frequency sweeps to listen for peaks and dips - there is no requirement for a sweep to sound flat to your ears.
Listening to a sweep can tell you the frequency (and with some exercise, also the q-factor) of a resonance, but it does decidedly
not tell you whether or not that peak should be reduced / whether that dip should be filled in.
Case in point: imagine an absolutely flat loudspeaker in a perfectly anechoic room - listening to a sine sweep on this loudspeaker will still create resonances in your ear depending on which angle you turn your head. We can measure those resonances! That's what the HRTF is. In the absence of context, you may or may not be able to actually hear those peaks when listening to a sine sweep - because the resonances are real (your ear shape creates them) even though the loudspeaker itself is completely flat.
You can find the frequency of peaks with a sweep, yes, but then use broadband signals (i.e. music) to find out whether those peaks need to be removed or not.
Peaks can be audible in a sine sweep and are expected, that in itself is not something that needs to be corrected.
That's actually not all that surprising! The rule of thumb is that in the top octave (above 10 kHz) the exact frequency response isn't nearly as important as it is in other frequency ranges, and it's mostly the total energy in that band that matters.
Which lines up exactly with your own experience.
I was actually surprised by how much the sound pressure on the B&K 5128 (The type 4.3 ear simulator) deviated from the sound pressure measured on humans.
It's marketed as a more accurate test fixture, but these tests don't support that.
For all over-ear headphones that I've tested, the Type 3.3 ear simulator gave more accurate results (read: gave results more in line with what we measured on actual humans) in the midrange and at high frequencies.
What was less surprising is that At low frequencies both ear simulators deviated from what we measured on humans in that they over-estimated the amount of bass. This is easily explained by the headphones achieving a better seal on the regular surface of the ear simulator's "cheek". This is why headphone manufacturers use leakage test setups (adding a controlled amount of leakage to the test fixture).
Something like this for in-ear headphones (the color-coded plugs can be removed and will each introduce a known impedance to the leakage path):
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