Sort of off topic, but my perspective here is of a headphone only audiophile. There is virtually no headphone equivalent of this discussion, since the design sophistication of high-end headphones has just recently exploded such that there have been really big improvements in the technology. Also in IEM design. There is not much of any "old school of classic products" in this design area going back more than 10 or 15 years or so.
There is the general feeling that the latest technology in planar magnetic headphone designs are in fact drastically better than in the past, and the oldest "old classics" are designs like the Sennheiser HD800 ring driver series. The latest big thing in headphone (and IEM) design is the use of the Heil driver air motion transformer technology, which I think is a true breakthrough.
Another big difference is the great difficulty or impossibility in the hobbyist refurbishing beat-up old headphones and IEMs, or in modifying them with new drivers, etc. That just isn't generally practical in this area of audio. So it is unfortunately apparent that headphone audio offers less than loudspeaker audio in the way of direct participation in engineering and modification and refurbishing, in getting intimately involved in the hobby.
In my opinion the major advantage of headphone systems is that they can offer sound quality in $10,000 to $15,000 systems better than speaker-based systems up in the $100,000 region, with the important exception of natural imaging and sound staging, where speaker setups always have the advantage. As they say, life is a series of tradeoffs.
