Expecting Rain

I'm loving the collected transcriptions of the "sermons" at the end of the book (I skipped ahead to read them, but loving the books overall).

So there's a lot of new information about Caribbean Wind in this book. Maybe this was already known, but I was surprised to read that the Biograph take is actually earlier than the one from the Genuine Bootleg Series, and the Biograph version was never the one considered for the final version of the album.

Which chapter(s) cover Caribbean Wind?
I saw the recording/rehearsal schedule in the appendix mention a take of Caribbean Wind taking place at Rundown Studios and I'm trying to figure out if this take is one of the released or whether it's still in the vaults...

Yes, the rehearsal version released on Trouble No More is from the Fall 1980 Rundown rehearsals. According to the appendix, it's one of many recorded in September and October (discussed in Chapter 8 of the book).

The next Caribbean Wind studio session listed is from March 31, 1981 at Studio 55, which I'm guessing includes the Biograph take (Chapter 10).

Then there were multiple takes on May 1 at Clover Studio, one of which is the widely bootlegged version from The Genuine Bootleg Series (Chapter 11). It's interesting that these were the takes that would remain in the vaults. Maybe they're saving it for a possible future 1980s Bootleg Series release, along with the original Angelina.

There would have to be right? It's the only way that all the 1981 omissions make any sense.
A 1980s bootleg instalment, that covers 1981-1988, with Tell Tale Signs picking up from
O Mercy through the Mod-Bob years. I would be hugely excited about seeing some of the
1983/1985/1986 stuff divested of all the production debris. It would hold a few revelations
and would likely become the go-to 80s Dylan collection, especially the murky 85-86 window.
Just the KOL sessions, properly unearthed, would be worth a disk.

I am extremely disappointed to read in the Notes that Jim Keltner was the only band member Heylin spoke to for Trouble In Mind. Tim Drummond may no longer be alive, but everyone else is, so talking to the others (with the new knowledge gained from the session logs and live tapes) should have been (obviously) high atop Heylin's to-do list. Instead, he mostly relied on older interviews already published by others. So it seems that this was a quick bang-out job timed to coincide with Trouble No More. I have only thumbed through it, but I see a lot of stuff I already know and very little that is new to me (I gathered a lot of available articles regarding the gospel era several years ago for a possible writing project). This was an interesting, productive, and controversial period of Dylan's life and career and it deserves far better than a mere compilation of already-available material (with a few new facts and transcriptions of the raps tossed into the mix).