GibbinR, your experience doesn't match mine. I use annotations for the same reason, and don't loose annotations. On the rare occasions I have, I've been able to track the loss to another problem. This is usually a corrupt database. And your description of the behaviour matches this. Losing data from the database after powering off is usually because part of the database is corrupt and wasn't saved.
As you are a heavy annotations user, I would recommend updating the latest firmware. Kobo has done a lot of work on the annotations. They added a second view to the annotations list, filtering by type, sorting by location and date created and fixed a lot of the bugs. One of the bugs fixed is that the chapter the annotation is in is correctly recorded and displayed when the annotation is made. Unfortunately, the big bug left is that the chapters are lost when the book is reopened. This has been around for a very long time and you will see it with 2.8.1.
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