The longer the sinc function, the sharper the transition band. Trading off filter length for a somewhat less steep transition band and still maintaining adequate image rejection is a common engineering compromise. Going too far with the compromise could lead to problems, of course. I'm sure there are examples on this site of good and bad implementations. For example, this was looked at in some detail in ASR's review of the Chord Mojo.
If the recordings you listen to are properly band-limited, I would not be too concerned about what my DAC is doing in the vicinity of 20kHz or above.
Unless you're a bat...
There are several things to discuss here. Better sinc function equals better brick wall, yes. Perfect sinc equals perfect brickwall with infinite stopband attenuation. The basic thing being questioned by Rob Watts of course is how sinc implementation affects the true time-wise amplitude reconstruction accuracy, rather than phase-amplitude plots in the frequency domain. Implicitly we are discussing the relative importance of timewise reconstruction vs. phase-frequency measurements. Filter design has used the latter as its starting point, hardly surprising as the Nyquist criterea starts with a frequency domain constraint, and that is how audio engineers have come to think; there being no great potential in analogue systems, in the linear region, for time domain problems not reflected in frequency domain measurements. Digital is potentially and probably IMO another story. Watts clearly thinks so.
Second, the actual filters used to approximate correct ADC anti-aliasing and DAC reconstruction are many and varied. Not all are closely based on a sinc function time domain result anyway.
To essentially re-state, the DAC filter can be seen as an anti-imaging filter or a reconstruction filter. In reality it is both. Both functions are potentially important. The first has had the emphasis in engineering thinking, historically.
Third, then, and most relevant here, is that the superposition of sinc functions at the sample rate is only perfectly accurate if that sinc function continues indefinitely in time both ways. I'm assuming, as Keith Howard was, that the DAC filter is indeed based on a sinc or very similar td function. Anything else is only a loose attempt to fulfil the Nyquist-Shannon reconstruction criterea, although it may have merit. For truncated (real world filter) sinc, reconstruction will be entirely accurate at precise sample time, but will be inaccurate, by a complex function, and to a degree not easily determined, at times other than precise sample times. The Keith Howard article explains the essence of this well.
The whole issue shows that digital audio will never be absolutely perfect and never can be. It is rather about 'how close can it be?' and 'how close is it now?', 'what would possibly improve it further in current practice' and 'is it good enough for your purposes now?'.