I think there definitely is a difference between $50 headphones and $200 ones, it's not like HDMI cables, you can actually see that the hardware you're getting is more complex and exotic.
Like IEMs with multiple drivers per ear, that will have to sound better than a $50 single driver one.
Well multiple drivers IEM can sound lounder with less distortion, but really our ears are not good enough to pick up on these minute distortions. Measuring equipment could, not our ears. The effects of EQ are easier to pick up by our ears than these minimal distortions. I had listen to a variety of IEMs throughout the years using different technology like Etymotics ER4, UE TF10, Shure SE530, Sens IE8 and Audio Technica CK10 and CK100. All you need is a good fit for consistency as well as comfort and EQ it to reference level or the sound you want. They all are very good, can't go wrong with any of them as long as they fit you. They all sound different but can be EQ to sound the same.
And EQ settings might make cheap headphones sound better but they skew a song's sound away from what the artist originally intended it to sound like
Unless its a binaural recording, most records are for loundspeakers reproduction, just by using headphones or IEMs will make the sound not to the artist original intention.
EQ is used to correct sound reproduction so the sound is to the artist or the recording engineer intention. Loudspeakers, headphones, IEMs all need EQ. Loudspeakers might get away with room treatment (but still it's easier to use combination of EQ and room treatment), but headphones and IEM forget it. Those need EQ surely. That's why the best way is to get custom IEM, they'll tune the sound for your ears, so you don't have to do it.