Generally I can certainly attest to the fact that I haven’t given high-res music files much of a thought these latest years, other than 2L recordings, but whether that’s attributable to the technological advancements made in jitter reduction with DAC’s as of late, as drawn out by the OP, I can’t say. Mostly I believe high-res files have sounded drab and downright uninspiring (again, except 2L files). The DAC I have used until recently saw the light of day around 2013/14 - does that even count as a more recent level af DAC-development? I guess not.
Nevertheless, my new DAC acquisition isn’t a new item by any stretch of the imagination (though it is upgradable, with some now awaiting), but rather a Danish all out development with incept date around 2012 - bought used, even though the model is still attainable as new. Former Orpheus top model DAC (back in the day priced in Denmark around $45,000) was the measure of performance to aim at during development.
Anyway, we’ve compared this Danish DAC/preamp of mine (priced new around $10k), not upgraded for years, to a very recent DAC/streamer development, the Auralic Altair G1, to see how a mid-priced still "wet painted" (i.e.: 2nd half of 2019) DAC might compare to an older high-end design. Is it representative at all, this shoot-out? Well, it’s one very newly developed, reputable brand DAC vs. an older design (known to few) - it HAS to be representative to some degree.
Long story short: old high-end design wins hands down. I guess that’s what an excellent analogue output stage, power supply, clock(?), and possible even a well thought out digital volume control implementation does - some years on its back be damned. What is jitter reduction and overall DAC chip development in the face of these factors? Not to say they aren’t worthwhile.
I had higher expectations of a new design, much lower priced even (to a new-price item of named alternative), and I truly had my eyes set on this route, also with the advantage of the latest streamer advancements (and in this regard, boy have they come far). And yet, back to old PC-based playback, which in many regards is a pain in the a**, but it’s a price I’m willing to pay with the sonic outcome "old Joe" delivers - at a cheaper used price even.