Earlier quoted context omitted.
You say share as needed, but I’ve not found a great way to just grab it to the clipboard or get the file handle from there. My go to workaround is to screenshot, annotate, screenshot the annotation tool into clipboard and paste that. (I know)
The two ways I do it are: 1. If the program I'm trying to share with is available in the Share control, I use that. 2. Since I already have a Screenshots folder in my dock that displays as a fan, and is sorted by most recently added, I click "done" on the annotated screenshot, then I can click on that folder in the dock, and it's right there, ready to be dragged into any other application.
I know pretty much every other combination of screenshot shortcut mentioned here, but this workflow has irked me ever since they added the annotation tools. I can work with this, thanks!