Define file's position on Timeline: add static(?) infographics to visualise selected option
Just a quick idea: could be an option to somewhere embed Illustrations that visualise how you are going to position your new file on the timeline.
Rough sketch:
Does not have to show up immediately, but there could be a "?" - icon or the question "Where will my file be positioned?" and if you click on it, the illustration is displayed. Probably requires some good graphic design / illu skills, because otherwise it will be confusing rather that helpful. There are also some more complicated cases, where it depends on how and when you added the previous file.
But generally you will be able to choose from a few different options in the future: synchronise will come soon and I think extracting the original recording date (#922) will also be an nice option, especially if you record with a tablet or smartphone where usually date and time are set properly (should be tested for live annotation). Those static graphics could be helpful to illustrate what each option will do.
Question: I'm thinking of static graphics because I suppose that everything else is too complicated, but maybe that's not the case?