Totally agree regarding point 1 - if you could enter a path mask for the CLI selection, you wouldn’t need it, as I think about it a bit more. Point 1 was more about being able to select the location in Conversion Tasks > Expert.
In terms of how to expose point 2, I think I’d accomplish it like this:
When a user selects Manual / CLI in the expert settings, a text field appears below it allowing the user to enter a path. File Path Mask probably isn’t the friendliest name, but maybe something like “restrict to only these locations.” There should be a plus after the text field to allow you to add an additional location.
If the variable approach is easier, I guess it’s a matter of setting up what variable corresponds to a given conversion task. I the case of Plex, and how I’d use it, it would probably be “%~p1” - the path of the file.
Really appreciate the attention to this!