Has anyone here listened to more expensive headphones, that are very neutral, only to find the listening experience being degraded because of that fact?

If you look at it from a Gestalt perspective, having so much detail and the voice separation being so clear, it's harder to follow the music as a whole. Instead, you pay much more attention to the individual notes, and the sound itself, rather than to the music. It's like paying attention to each pixel on screen rather than on the picture displayed. Or reading a sentence as individual words rather than a semantic whole.

I find that I can't help listening like that, because each voice and detail is so clearly presented, that it's only natural to focus the attention on the details
As with cheaper headphones, you don't get the specific details bombarding you all the time, so you tend to concentrate on the entire melody, rather than the individual notes. With expensive audio equimpent that are neutral, no harmonic noise, the music seems fragmented and lack cohesiveness.

Now, the Ibuds can be too blurry and you can't hear a lot of the voices as they are all mushed together into one thick strand of sound, but on the other extreme, perfectly neutral headphones can give you an accurate representation of what it sounded like in the recording studio, but that seems to make the music boring.

What are your thoughts on this?

@HTS

With "expensive" headphones (senn hd595) I'm more aware of music defaults, but it doesn't degrade listening experience.
It might degrade it, if you become a perfectionist, seeking endlessly the best sound, without taking much time in appreciating the music.

Saying you'd rather listen with cheap headphones, is like saying you'd rather be myopic than see the actual world.

In other hand some headphones might have sound too "sharp", that it might look unnatural.
This is especially the case with some n Ear Monitors with balanced armature (from what I've read, I've never tried one).
People say that they are "analytical". This might be great for techno, or electronic music ...

It all depends of the music too. A cheep headphone, can "blur" the sound, but you can't hear to anything "sharp".
But with "expensive" headphones, you can hear both "blurry" and sharp sound depending of what you listen.

Also most expensive headphone are not necessarily the best. Some model might just reflect some people tastes.
You might buy a "1000$" headphone not necessarily because it's more accurate, but just because you like a particular sound signature.