Reintroduce live annotation
This issue needs to be broken down into smaller issues. If you start working on parts of it, please first create a new to do issue (e.g. "add current time to annotate-input") for the specific part you are addressing.
Before the menu options for live-annotation are reintroduced (live annotation tab, menu entry for the timeline item on the projects page) there should be a few changes to the live-annotation-interface:
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The annotation input field should display the current time (with seconds!). Knowing the time is also important to later synchronise your video to the annotations.
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There should be a button that allows you to "save the current time". It might be better to even call that button "recording started". I would suggest that this button creates an annotation with purpose linking (! so it will be later visible in the Timeline later compared to the other live annotations), which says: "Recording for Live-Annotation session started at hh:mm:ss". Ideally you hit the record button of your video camera at the same moment. The annotation with the time information will allow you to position the video at exactly the same moment in the Timeline later, so your recording and your live annotations are almost in sync.
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There should be a "?" help option, which brings up an overlay that explains how live annotation work with the help of some graphical visualisations. I will try to provide a sketch for that. I suggest to explain it in 3 steps, with three graphics and you can step through these (similar to the adobe update information/instructions).
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This help overlay should also be displayed when you access the live-annotate screen for the first time and pop up every time until you select "don't show this again".