File | Export | Outliner Contents as CSV - only works when the outliner has the focus. If you’re not in outliner mode at all, that option is greyed out on the menu as expected, but when the outliner is visible but doesn’t have focus (say you’ve clicked on the binder or something), the menu option is available - it just doesn’t do anything.
File | Export | Comments & Annotations - only seems to export the selected documents regardless of whether the Selected Documents Only box is ticked.
…this maybe should have gone in the Bug Hunt section, but I’m open to the possibility that I’m just doing it wrong. 
The focus problems when exporting the outliner contents was already on the list to be refined, and I’ve added the new issue with the comments & annotations export. Thanks!