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I'd say best case scenario is you mod it and LOVE how it sounds. The scope is not an eardrum. Humans are not manufactured according to strict tolerances, we also have vastly different experiences, some are professional musicians, others work construction.
I also disagree considerably with the concept that measurements are == transparency. First you have the philosophical angle, what *is* transparency? Is it what you *hear*, or what *is*? Because if you can't hear what *is*, then how do you experience transparency?
In that same vein, one thing that bothers me about NwAvGuy's approach is that while he dismisses clearly better performing parts as "not worth it" (OPA627 for example), he also pushed the amp to the lowest possible noise floor imaginable, a noise floor so low that I'd say it's 20% beyond "not worth it". But at the same time contends increasing the slew rate to the max that Blu Ray can handle, is "not worth it".
So whats really not worth it? A noise floor and distortion figures well beyond human hearing? Or at least meeting the specified capability of blu-ray?
Point is, a human can be just as biased about how they approach being objective.
When it comes to headphones, your fundamental viewpoint has a lot of merit: Headphones are extremely difficult to reliably measure, because they require an accurate microphone to recapture sound (rare to nonexistant, much like accurate drivers), and the positioning and geometry is going to be totally different from your outer ear, etc. Transparent headphones are basically headphones that sound subjectively lifelike to you, given a "proper" acoustic recording. (IEM's are even harder to measure, since they bypass the outer ear entirely. This will make the experience match up with "real life" much differently for different people than it does with speakers or full-size headphones.)
However, amplifiers are different: An electric signal is easily measured with the proper equipment, and a transparent amp is one that amplifies the signal with as little distortion, noise, etc. as possible. This can be objectively measured very accurately, and it is, so transparency is well-defined here. A transparent electrical signal is simply one that measures well across the board, and there's no subjectivity or magic to it.
You can legitimately judge the transparency of an amp + headphone combo by ear, and your subjective assessment will basically trump any objective measurements for you (because of how difficult headphones are to reliably measure, and how much the headphone experience varies individually). With your particular headphones, a colored amp might produce the most transparent final output. However, you cannot accurately judge the transparency of an amp by itself via subjective means, because you can only experience it indirectly through inaccurate headphones. In the best case scenario (low-impedance and high-sensitivity headphones with a low output impedance source), you can look for differences between the unamplified signal and the volume-matched amplified signal. More commonly, the best you can do is ballpark it ("this amp sounds warm, given it's warm with headphones A, B, and C, and C is not known to be a warm headphone"), and objective measurements have the final say on the transparency of an amp by itself. By itself, the amp's signal transparency is a simple matter of objective metrics, and "sound" doesn't even enter into it, because an amp deals with electricity, not sound.
To sum it up, the unmodified O2 is essentially transparent by itself, but the final sound you hear is only guaranteed to be fully transparent if you pair it with a fully transparent headphone model. On the one hand, it's unlikely that you'll find a pair of headphones that matches your ears perfectly. Even with extreme high end flagships, you can only get closer and closer to the pot of gold at the end of the rainbow.
On the other hand, it's similarly unlikely that adding an extra hardwired layer of error via a colored amp will change this situation. (An easily configurable software DSP would be a much better bet, unless your enjoyment of trial and error soldering with random components outweighs its inefficiency for you.)
Instead, what the unmodified O2 guarantees (under most conditions) is that it will present headphones as they actually are rather than presenting the sum of two inaccurate components. It removes a source of error from the equation, and for me this greatly simplifies the matter of finding the right headphones. (Once you mod the O2, you're fundamentally changing it from "just an amp" to an "amp plus analog sound processor," which reenters the grueling world of trying to find synergy with a particular set of headphones.) It won't compensate for errors your headphones make, but it won't pile on and magnify them either. If you want to use or try multiple sets of headphones with different sound signatures, that's really the best thing you can ask from an amp.
I should also note that it's extremely important for headphone design that amps like the O2 (and Violectric amps, and Benchmark DAC1 amp, etc.) exist: Headphones themselves have long been the weakest link in the DAC+amp+headphones+ears chain, and neutral amps give manufacturers a concrete reference point for engineering and tweaking the sound of their headphones.
On a side note, the emphasis you place on one objective metric over another will indeed be influenced by subjective bias. I will concede that the designer might possibly be putting too much emphasis on an out-of-this-world noise floor beyond the point of diminishing returns, such that other metrics may be suboptimal in extreme situations (like the max slew rate you mentioned). Still, that's a more nuts and bolts issue rather than an issue of principle. At the very least, you know you won't be hearing much hiss or hum from the O2.
Rather than a serious flaw, I'd consider it more of a minor issue to consider addressing in future designs (much like or even moreso than the input overloading issue), given any other known sub-$1000 range amp with a theoretically better max slew rate is going to be crushed on more audible metrics like frequency response, noise, or distortion.