I wonder if Dylan himself had any interest in this kind of sequencing. It's the kind of thing the producer would think about, whereas everything we know about Dylan suggests that he prefers a more accidental way of doing things. I don't think there's any reference in Chronicles to planning the running order of his albums.
I think Dylan was acutely conscious of every last detail in terms of how he presented his music, and particularly so in the 1960s when he was white hot. There's a line in Chronicles in which he says: "I try to use my material in the most effective way". It's a very simple statement and almost thrown away, but it's indicative of a sharpness of both purpose and vision, I think, and which I'm sure included decisions about sequencing and running order.
Apart from his deference to John Hammond at the very start of his career (and whom he still refers to throughout Chronicles as 'Mr Hammond' ) he never trusted producers, really. Remember, he sacked Tom Wilson half way through the sessions for Like A Rolling Stone - and Wilson was never even told why. The closest he's come to any real trust with a producer was Lanois, but even about him he writes somewhat sharply in Chronicles: "I was incapable of taking a lot of his emotional trips seriously." He now produces himself under the name 'Jack Frost', of course. He also sacked Albert Grossman as his manager when their contract expired circa 1970 and he never appointed another manager, opting instead for an array of advisers (led today by Jeff Rosen) and taking control of all major decisions himself.
Yes, I think he does like an ''accidental way of doing things'' in that he likes to leave room for spontaneity. But that's very different from being haphazard. I suspect he's rather carefully nurtured the whole 'accidental' notion in the same way that Neil Young has. In reality, his focus is razor-sharp, single-minded and all-encompassing of every detail. And - apart from the lost years when he stumbled through the 80s - it always has been.
Sorry, Des. Yes it has indeed become another Bobby bloody Zimmermann thread and I could spout Dylan theories all day if you let me, I'm afraid!