The first thing is, and I learn that every time with every new headphone: they are never impressive, just different.

Give it a week or two of heavy use, don’t switch back to the Grado, and your brain will adjust to how the XS sounds.

THEN switch back to the Grado, and either learn that it sounds worse than you remembered, or that you still like it and don’t really care for how the XS does things :)

I can’t tell you about this specific jump in quality/price, but about a similar experience.

I had an AKG K701, went into a store and tried a random headphone with a ludicrous price tag - 5500€.

This particular difference was so mindblowing that I stopped listening to music on headphones entirely for about 12 years, until I could afford my own hd800s, hoping it is „good enough“ compared to how I remembered this specific headphone. (Turned out to be a Stax, maybe SR 007 or 009)

The HD800S is worth it if you care about stage and natural timbre, it’s not as precise as some planars in its price range, but just smooth.

There are 2 complicating factors I think…

1. it’s a sliding scale, not something where you would say, headphone x doesn’t have that yet, but headphone y definitely.

I have headphones that seem to have that quality more than others, but this is also dependent on how a headphone stages - sometimes it feels like I noticed certain elements mostly because they appear somewhere else than where I was expecting them

2. the ear is a funny thing… once you get used to higher quality gear and hearing things that you didn’t hear before, you train your ears and will also hear those things on lesser gear, to a degree.

I know this doesn’t answer your question, but hopefully inspires a bit to do you own experiments with the type of music you want to listen to 😊

Look at the Focal Bathys, it basically uses this idea: have a DAC built in because Bluetooth, but also allow the headphone to be used with a usb cable to receive a lossless, digital signal that the built in DAC also handles.