Someone didn’t check their arithmetic! I was surprised also. Maybe this is a case of follow the money, where this retailer focuses on selling front end source equipment rather than speakers. 
There seems to be differing cross-Atlantic views on whether to focus on the front end vs transducers. I believe there are multiple effective approaches and “it depends” on what one wants to designate as the initial anchor/focus of their system. For example, the Magnepan LRS, Elac Uni-Fi, and Senn HD650 all sell at relatively lower prices for their performance potential, and need to be paired with powerful, generally higher end gear in order to thrive/fully deliver. On the other hand, budget Schiit stacks are found in chains with kilobuck cans as you stated.
This is a major factor. Relatedly, historically headphone technology/design innovations/updates seem to have occurred not as fast as electronics. However, the last few years in headphones have brought us an abundance of latest and greatest, some novel headphone innovations: ZMF original dynamics and Focal high-end cans in 2016, followed by MySphere open design, RAAL SR1a ribbon drivers, and HEDD AMT.
For an analog turntable setup, there are multiple mechanical components and moving parts: the table, tonearm, stylus, phono stage, even before getting to amplification. On the other hand, digital involves the relatively more simple streamer/CD transport and DAC chain (see dongles that can be connected to a phone). Maybe the higher mechanical complexity for analog puts more of an emphasis at the front end, and added cost. Granted, for any type of setup, getting any sound to play can be accomplished for cheap, with higher quality components often bringing better sound.