Yes, actually. If it were true that I preferred a less accurate amp, a less accurate DAC, etc., then yes, I would rather listen to that than the more accurate chain. It comes closer to satisfying the goal, which is to maximize pleasure.
Fortunately, we don't really have to worry about that with electronics, as 99% of them are 100%(audibly) accurate, and I don't care enough to spend money testing my preference for the few that aren't. If electronics were as all over the place as speakers, then getting a great sounding system might be a total crap shoot.
For loudspeakers, though, they can be different enough where - for some - it might be worth it to explore less accurate options in pursuit of maximizing preference. Not for me, though. Other than maybe dispersion width, I'll be making my purchasing decisions based 100% on both accuracy and preference, as Toole's science says they are one in the same, even for classical. I'll trust that I'm normal. It's too expensive to try and find out if I'm not.
Again Toole/Olive's science tested for preference, but the test showed that the most preferred loudspeakers were the ones that were the most accurate. You've put forth the hypothesis that these studies don't apply to classical music, and you've come up with some reasons why that might be true, but I don't see any real evidence to support that it IS true. Remember, they tested with classical music, and the trends were the same.
What you're saying might be true, but you need to show that it is, in my opinion.