A $2,000 barely running junk car is still many times faster than any human can achieve on a bike.

You need space, room treatment, and a fixed listening area for high-level room audio solutions. I can bring a pair of cans to anywhere I visit. Even with my desktop setup, I can listen at my desk, sofa, or armchair with an extension cable.

FWIW, I think there's plenty of differentiation at the high end if you know what you are looking for, and willing to build an appropriate system around a pair of high end headphones. You can also make $500 speakers sound really good with treatment, so the cost point isn't clear either way.