: How can we make compiling release notes less chaotic? Each of our software releases is accompanied by a set of release notes, which include short descriptions of the following: new features,

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I'm at a different company now than I was when I asked this question, but the new one had the release-notes problem too. Here is how we solved it (at doc's instigation):

When a bug is filed, if it's customer-reported or customer-facing, the "needs release note" box is checked. (There is a triage team that reviews these and might change this, but this is the starting point.)
When a developer fixes a bug, if that field is checked he writes a short release note right there in the bug (there's a field for it). Reasoning: he just fixed it; this is the best time to capture what the problem was.
QA reviews/updates the release note as part of bug verification. (Developers sometimes write "internal" descriptions, such as that the problem was with such-and-such mutex being held too long instead of saying that something froze; the testers know what symptoms and changes they're looking for and can verify, so they can fix some of this.)
Near the release, people in doc make a pass over all of them to make sure they're coherent English. (There's a report to find all of them; it's the same report that feeds into the final document.)

Obviously if somebody decides late in the process that that bug needs a release note after all, this breaks down. But for the ones we know will (or probably will) need a release note, we try to capture information as early as possible and improve it as we go along. The incremental cost to the developer at the time of fixing the bug is very low, while the cost for anybody trying to figure it out weeks later is much higher.

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The idea of letting the developers write the notes will shatter on the cliff of reality. Most developers don't want to write them, so even if you force them somehow, you will only get a mess and not a note. Just for the record: I am a developer.

What you can do is just improve your existing workflow a little bit. A little bit often does wonders and you will never get a perfect workflow anyway.

Which means, there will always be some back and forth, you already know that. So best workflows are automated, because they skip that damn human factor. Try to automate as much as possible. (Never send a human to do a machine's job.)

"annotate with 'affects docs'" - skip that. That's relying on humans and therefore error-prone. I bet you have a priority level on bugs. Define that bugs of the most upper two levels get annotated automatically with "affect docs". Do you really care about the other ones? Developers don't.
"Toward the end of the cycle ..." - Ouch! You know what happens if you shift a task at the end of a cycle, so why do you do it? You get the list of relevant bugs now automatically. Have a meeting (a real one, not a lame one) every week, every two weeks, whatever, with the project lead. Go through the list, ask your questions, get answers.
"... not sufficiently illuminating" - If things are still unclear (within that one week or two week rhythm) ask the developers. You can never avoid speaking to that lousy pack from time to time. It's a shame.
"Iterations happen" - Development is iteration. By its very definition. You'll never get rid of that. Embrace it. It's a cure, not a disease.

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Compiling release notes is NOT the job of a single author. It's ideally part and parcel of your source control and project management system. Your developers would have a set of automated tests for all reported bugs and documented features, and any necessary changes would require a change in said test, which could automatically note a change for the release notes.

New Features would mean new tests, which happily could have supporting documentation. New Test -> New feature added to release notes.
Changes to existing features mean some old tests stopped working. Change a test -> note that "action X and Y no longer does Z."
Bugs, after being recorded internally and having a test written to demonstate the error, can be identified and marked as closed once a "known-bad" test no longer breaks.

Consider, btw, how two games do their release notes.

Eve Online does release notes in mammoth lists, introduced by blog posts for major new features and a discussion forum where changes are suggested. Notably, bug fixes are NOT detailed, as there's no public bug repository.
Minecraft, on the other hand, has a public bug list and includes links to their actual bug database for resolved fixes.

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First off, technical non-writers make better technical writers, than non-technical writers do. They usually can write in a way mostly understandable to layman and factually correct (as opposed to non-technical writers who'll often write something perfectly clear, but completely wrong), they just need to be asked to do so - they won't, if they don't know they should!

Instead of non-technical people assembling the notes, have technical people tasked with assembling them in a relatively reader-friendly manner. Best, if everyone in the team wrote short release notes on everything they did in person, every bug they filed, asked to explain it in relatively non-technical manner (typical to release notes - they know what release notes are). It's 10 minutes of work per month, and you have a good preliminary draft almost complete.

Only then have the non-technical writer edit the draft, making it pretty, correcting errors or smoothing out still too technical language. If something is hard to understand, consult, perform the usual back-and-forth, but the number of these cases should drop to 2-3 per iteration from dozens. Simply, instead of asking the non-technical writers to reach across the chasm to the professionals, have them meet halfway - essentially, everyone becomes the writer, but you're getting one good editor.

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