I'm with you on pretty much all accounts.
What I suspect, & I don't really have anything to base this on but my own intuition, but I think that the Wilburys records kind of skewed Dylan's ability to criticize himself, & I think he tried to record Under the Red Sky as casually as they did Vol 1 & 3, only he didn't have the other guys chipping in. Because none of those songs are as good as, say, If You Belonged To Me (which I think is Dylan's best original from those years, personally).
And so I think that, like you said, Good As I Been & World Gone Wrong sort of realigned things for him, & gave him a much different way of approaching music, as the traditionalist rather than the "anything I put down on paper is gold" elite songwriter. But, to that end, I think the recordings were intended more as therapy than song recordings, & they were all done in a day or so at Dylan's house on one set of strings. That's why I say they were half-assed. If he were to record those songs today, they would be tour de force arrangements, like the songs on Tempest. But he just didn't choose to put that effort into them. Which is fine, they're still brilliant albums for what they are & for what they represent & for what they accomplished.
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