Whew~ Just read this whole thread. Lots of interesting and informative comments.
I can say I've certainly noticed improvements in a long list of DACs I've owned and upgraded over the years. Around 10 years ago, I started out with "mainstream" DACs from the likes of FiiO and JDS Labs, etc. like everyone else and slowly and incrementally upgraded every few years until making the big leap to the Chord Hugo and Mojo back in 2016.
With every upgrade, I heard a significant improvement but the jump to the Hugo was huge as it was with the Mojo as well. I still own them for different usages even after making another big leap to the TT2 along with the HMS. Again, the improvements were very substantial although not quite as mind-blowing as going from the "mainstream" stuff to the original Hugo around 6 years ago. That was also around the time I went from midrange ($500~700) Sennheiser and AKG cans to the HD800S and the JH Audio Layla CIEM.
My foray into summit-fi started only a few years ago but I'm getting into it in a big way after deciding that I don't want to really put my time into collecting guitars and related equipment or even playing anymore. Just got tired of playing the same ole licks over and over again and I just don't have the time, energy and the enthusiasm to learn new things to play or get better at the instrument. So I sold all that stuff to get started with this audiophile addiction.
Having been a cork-sniffing guitar tone connoisseur for decades and having worked at major guitar companies and even owning a boutique guitar and amp shop for some years, I can say my ears are tuned to hear micro details but, at the same time, I'm also of the opinion that at a certain point, the law of diminishing returns really kicks in and the value quotient really takes a dive as you get into the stratospheric price levels. Also, because our ears are all so different and there are so many subjective and intangible, i.e. unmeasurable, factors involved when analyzing sound, one's own intuition really is the best guide to decide what works and what doesn't.
I'm sure that the DAVE or Bartok/Rossini or this MSB DAC I learned about for the first time today (I guess the counterpart of something like Wilson Audio speakers?) sound "better" than the TT2 but I also know that these are things I really don't have an interest in pursuing and won't have the means to get for many years to come, if ever. I'd love to hear them someday at trade shows or a store when things return to normal and something may indeed trigger an impulse to start another upgrade path but the thought of paying double or more over what I have for what may be 2 to 5, maybe even up to 10% improvement to my ears should shut down that urge quickly.
I have the SR1a and the LCD-4 with the 1266 TC coming in very soon and I already feel like that it's more resolution, detail and realism than I will probably ever need. Sometimes, I feel like the system I have now sounds even better than "real", if that can term can even be properly defined. In fact, I'm now looking to go in the other direction with something more "lo-fi" and not as precise and analytical as what I have now with the ZMF VC and a tube amp to enjoy classic rock, blues and roots-oriented music in a more "authentic" manner.
Having been a rock guitar player for decades, I've come to appreciate terms like grit, phat, dirt, raunch, soul, feel, vibe, "musical", etc. that are decidedly intangible. I'd like to be able to "hear" and
feel these things as I have heard from vibrating woods, analog processors, and tube gear when playing the guitar or making recordings at home or in the studio. It will be interesting to see if I can experience these things in the audiophile world as well but I'm sure that's why there is a very sizable contingent who swear by vinyl, analog and tube and describe digital as "cold" and "soulless". I'm not for in either camp but I can appreciate where they are coming from.
In regards to break-in and burn-in, yes, they are real but the amount one notices the effects or the improvements will vary depending on the piece of gear. It's obviously very real in the world of musical instruments like the guitar and other wooden instruments like the violin, piano, etc. Guitar companies go as far as to "age" the woods with a process called torrefaction - baking the woods at a certain high temperature in giant oxygen-free ovens. To a degree, this will make new guitars sound like 50~70 year old vintage instruments. Essentially, they are sucking out the inherent moisture in the woods and they "mellow out" and sound more "complex", as guitar players love to use the term, after the process.
The same goes for amps, cables, speakers, speaker cabinets, even wires in pickups or pedals, etc. Some guitar players get pretty crazy with this kind of stuff, changing the hardware material from steel to brass in the guitar bridge, only using the cheap 99-cents carbon batteries instead of Alkaline batteries in the pedals, using 15-foot cables to connect pedals that are only inches apart because they "sound better" that way, removing the screws at the bottom plates of pedals and wrapping them with rubber bands, etc.; it just goes on and on. They'll passionately argue on guitar gear forums about certain caps or transformers in the amps, the magnets in the pickups, the materials used on the cones of the speakers, solid wood vs. laminates in speaker cabinets, blah-blah-blah. You think it's bad here; you ain't seen nothing until you see what they talk about. Haha.