O.P., think about it this way:
When a transducer plays back sounds, it can't do it perfectly. It adds distortion related to the sounds being played - harmonic distortion, intermodulation distortion, time-based errors as a result of overshoot and a less than infinite transient response, etc., etc. that are all not part of the original signal. As these distortion products get loud enough, they mask details because the noise floor at a given playback level rises and can even go significantly above those details, to the point where when you measure the driver, say music with a particular sound "detail" playing at negative whatever dB and the same music without that detail, you can't find a statistically significant difference. Then, the sound is effectively not produced at all. And since our ears are particularly insensitive compared to measuring equipment, that threshold is far easier to reach for us than for our microphones...
Want an example? How about this one:
Not exactly fair, is it? But look at how fast the HD 800 driver responds to the DC impulse of the square wave - near instantaneously. The Lady Gaga instead takes its own sweet time, slowly responding to the impulse and taking about a third of the time between the impulses to even reach the maximum extension. Oh, yes, the HD 800 is distorting too - it can't produce a constant pressure wave... But it's behaving like a critically damped (i.e. optimally) transducer should, compared to the massively overdamped Lady Gagas. If you're playing other frequencies on top of that, for example, the distortion created as a result of reproducing the low frequencies is going to be in the harmonics above the fundamental low frequencies, and right smack-dab in the middle of the midrange and treble that you want to hear the detail of. So you've got all these distortions that aren't supposed to be there, and as they increase they make it harder to hear the original signal - until you reach the point where you can't any more - and eventually, measuring equipment can't distinguish it from the noise either. At that point, it can be said that that detail - that particular change in voltage over time - isn't reproduced at all.
So yes, details can actually be not reproduced by transducers - that happens when they can no longer be distinguished to a statistically significant degree from the background noise.
I do agree that some headphones with extra emphasis on the treble seem to resolve more but don't necessarily - again, it depends on the distortion products. For a lower distortion, flat headphone, you might actually have a higher signal to noise ratio in the treble than one that emphasizes treble over the lower frequencies but has relatively high distortion within the treble itself. Lower distortion products may be masked by the dominating high frequency response, but distortion products within the treble itself will be emphasized as well. The reverse could be true as well - it all depends on the particular examples. It's really any enormously complicated field, and I'm not even going to begin to explain it because I don't even fully understand it myself.
Just realize that it's not so simple, so black and white. Much of what we're down to is probability and statistics. You know, eventually there's going to be white noise produced by a random thermal noise generator that conforms exactly to Beethoven's 9th Symphony...