Coffee Music
100+ Head-Fier
Unlike you, I had a mental breakdown because they were too good.
No wonder you take breath-taking pictures.I think Headphones and DAC/Amp behave similar to Lens and Camera selection.
As a photographer we always strive to gain great detail, contrast with as little distortion and imperfections as possible with the imagery we capture. I have several lenses which make the Empy seem cheap, designed to work with high quality, high MP cameras. They make my life easier as I have to spend less time processing images dealing with those imperfections.
If I take a cheaper lens and use it on a cheaper camera body that resolves to say 16-20mp sensor, it can look very good. Take that high end lens and stick it on that camera and the image will look a little better but not fantastic given the price difference. But on a camera with a bigger / better sensor the lens really shines and produces bags more detail and excellent micro contrast.
However, there are downsides with the better cameras... they do need those better lenses. If you pop that cheap lens on them they will reveal / magnify all the imperfections and weaknesses of that lens. Most likely will look soft (focus), especially on the edges and corners with poor detail and plenty of aberrations. This is why you tend to buy the best lenses you can afford as they'll allow you to upgrade camera later on without having to replace the lenses.
Headphones and DAC/Amp combinations seem to work the same way. You could have the best DAC/Amp in the world but if you use budget headphones and speakers it will never impress. But, you could have the best headphones in the world and they'll only reveal the maximum level of detail that the DAC/Amp is capable of... no more.
Consideration has to be given to the whole chain to maintain a good balance and not to sacrifice one element over another. That includes cabling and power.
A shorter version of what you're saying is that higher-end model is more revealing of perfections and imperfections. And pairing them with lower models reveal more imperfections than otherwise. While that is mostly true, some products like the HD 600/650 will rock your heart when paired with top gears