Well I have my Noble K10U IEM's & my older Shure SE846 IEM's and yet my reasonably priced all-in-one KEF LSX speakers are just as enjoyable and more so at times (in a small room).Yup, but i mean with speakers and a stereo amp as well as the phones and HA amp. Not many of us get to that level without multiple upgrades, but it would be nice!
Its "Emperor's New Cloths" much of the time now. I had a £1800 Hugo 2 as a DAC/AMP couple year back but my modest priced Sony ZX507 DAP (Japanese import) is just as good unless you have demanding headphones (to my ears anyway).
High-end audio is a money pit for those that want to spend IMO now. Paying for more like jewellery/uniqueness than significant jumps in audio reproduction. (Different for room audio systems).