Not enough time to answer this, but in response the idea of giving an audience what it wants or something else… . First, people often don’t know what they want. They also don’t know what they need.
As for Dylan, he was in the right place at the right time and offered up a “product” that was perfect for the times, which were definitely a-changin’. In the 60s, the fact that he did not have a “beautiful voice” made it easy for lots of singers to record his songs and not feel they were copying. They put him into the pop scene at the very same time he lived on a different plane, eschewing that scene.
There are so many levels of marketing taking place in Dylan’s career. In some ways, (people will cringe at this) he got a lot of media coverage by making outrageous statements (like someone of recent vintage) and gained a wider media power thereby. Look at all the photos he allowed to be taken of him throughout the 60s, too. He was a content creator simply by allowing himself to become “content”….
For half a century he continued to be a content creator, and became a Brand so that whatever he did was noticed, written about, shared.
The constant touring, especially the Never Ending Tour, 100 concerts a year for near three decades, was unique, too, because he was continually re-inventing. Most of the concerts were not only different playlists, they were also different interpretations of the same songs. All of this became “new material” … new content.
He’s got a great PR team (media connections), a great Brand, devoted fans… and Great Content. He earned it be continuously pushing boundaries and not resting on laurels. In point of fact, had he just rested on his laurels, the kinds of fans he has would not have hung around…