Out of curiosity, how much have you spent on those "at least" 5 CD playback devices (CD player/transport/DAC combo) over the two and a half decades?
A good amount, but not that much. I can't afford $ 50K or $ 100K DACs. Not that those cannot be worthwhile.
At what price point does a digital system match the rhythm and timing of "modest vinyl"? At what cost does digital compete with the very best (analogue) vinyl playback systems in sounding "natural" and "right"?
Don't know the price point where it starts. All I can say that my current digital, which I think sounds "natural" and "right" and has excellent rhythm & timing, is less than 10 grand including *all* components in the digital chain (ok, including the high-quality power cords the price point of 10 grand is reached). My preamp costs considerably more...
I made some decisions that some might find curious per pricing. My reclocker and the AES/EBU cable between reclocker and DAC each cost almost as much as the DAC itself, which is only $ 2,200 *). There is a reason for all this, it's not a fluke or silliness. The DAC can compete with multiply higher priced DACs *if* the entire digital environment is right. Good digital cables are part of that. For components, see my signature.
Since Sony released its' CD format, fantastic amounts have been spent trying to improve the presentation from that format. R&D should have resulted in lower retail prices over time,
It did, when it comes to achieving great quality. If some want to spend more to achieve SOTA, that is also fine and up to them.
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*) Part of it is that the DAC is direct web sale. As the designer explained, the same DAC sold via dealers would have to cost at least $ 6K, not just because of the mark-up, but also because a more expensive DAC would sell much less units. With the sales figures they have they can achieve better bulk price quotes from parts manufacturers. Regardless, the DAC can also comfortably compete with others far above a $ 6K price point, as I have heard multiple times myself.