"So we used timelines. This meant that every prompt for a period of about four years, she had to find SOME way of organizing it into a sequential thing-- timelines, linear narrative, biography, etc."
You know, this reminds me of a recent conversation about the importance of writing instruction. The use of graphic organizers has helped mold my kids' thinking into something that is more, well, organized. My DD is now able to write without one. DS clearly still needs a significant amount of more time with the graphic organizer to establish this habit of thinking. It sounds like with HK's daughter, the use of timelines helped mold her thinking into something significantly more sequential. These seem key tools for cognitive development, whether we cast it as writing instruction or not.
Just thinking out loud.
"DS is supposed to be using graphic organizers as part of his IEP, but I don't think that's happened."
Then you need to follow up on that with the teacher and IS. If something in the IEP isn't being implemented, don't simply try something else. Fix the IEP problem. If your experiments with Inspiration are successful, but all means bring it to the table, but don't abandon something just because it hasn't been implemented. Follow up.