“Lossless” digital audio playback is not analog audio playback.
The analog signal still has more information that no A/D converter, no matter how good, can digitize.
That's simply not true.
First of all you need to understand that every signal, doesn't matter if it's analog or digital, that is somehow processed technically always is bandwidth limited: lower frequencies below a certain limit are cut, as also higher frequencies above a certain limit. No real technical signal contains an infinite bandwidth from 0Hz to infinitive Hz. Impossible. And also useless. Nobody can hear sound at 1Hz or 1 MHz. Pointless to record, process, and store such frequencies. And also analog systems cannot provide all frequencies (Ever listen to some old phonograph? Very analog.)
The question is, where those limits are set. And not seldom when an analog audio signal is digitized the bandwidth is chosen a bit too narrow to reduce the amount of data. But that's not the fault of digital signals per se.
When in the 1980s CDs became popular, their bandwidth was reduced to the frequencies "what average people can hear." People with an extraordinary good sense of pitch can hear the bandwidth is limited comparing to a very good analog sound system playing an extremely good record at highest quality.
But this does not prove digital is always worse than analog. It just proves CDs were not always better than analog recodings (as they were sold.)
Besides the bandwidth you need to see is the sampling rate. As long as the
Nyquist–Shannon sampling theorem is fulfilled there is no loss.
So, when you compare an analog with a digital audio signal both having the same bandwidth, and the digital signal's sampling rate is greater-equal two times the highest frequency of the analog signal, there is absolutely no difference at all.
Where you get differences in digital is when you use compression,
so not using any .wav anymore, but some .mp3 for example.
But then we are talking compression, and not digital in general anymore.
And what you also have to distinct is your audio equipment. When you hear a difference between you digital and analog recordings maybe this is caused by your analog stereo equipment is very high quality, while your digital is cheap crap.
Last but not least the digital signal needs to be converted into an analog one and being processed by amps and boxes to be heared.
Those are all factors which can influence the quality of an audio signal, but to say digital is per se worse than analog simply is nonsense.
I kind of wonder if that guy is on to something about f-minor/d-flat though:
