His points are valid in theory. However, when it comes to implementation, the story changes.
First, for digital equipment to "smooth" the curve effectively, it must be well designed. Sure, there is plenty of equipment that is well designed and sounds very good.
But, second is the software. He does make the point about the so-called loudness wars. As digital sound engineers increasingly use higher volume and more compression, the quality of the recording declines. Similarly, some analogue recordings are poorly produced. Overall it seems that the quality of most analogue recordings is better than the corresponding digital versions, and even more so with more modern music as the loudness wars have become more prevalent.
So, if sound engineers focused more on producing great sounding recordings, rather than loud sounding recordings, I think you'd see that many more enthusiasts would embrace digital over vinyl. That's because the sound quality would be similar enough, but the digital versions are often easier to consume... like on the phone, in the car, over the internet, etc. In today's world, the sound quality problems start with the overly compressed recordings.
This compression issue and the "loudness wars" is the reason I strongly prefer vinyl. Even though I do occasionally listen to a CD or SACD, and I stream when a record isn't convenient.