I think my biggest concern about this feature is that it seems
engineered/focused on the use case "having a playlist of multiple files
the user wishes to store independent resume points within" which seems
to me not the most common use case for automatic resuming.
I would expect the general use case for an automatic resume is to resume
a file automatically when selected, but not necessarily for every file
within a playlist.
Is it really that common to have a playlist of separate podcasts and
books all partially complete?
I just feel we should be focusing the offered options and functionality
for the way the majority would use such a feature, and only add things
for the less common cases if it doesn't significantly complicate things.
All these options seem to complicate things. I think a simple auto
resume of "when a file is selected, resume it if possible, but never
otherwise, and store resume points only when a file is stopped" would
cover the vast majority of use cases (though very obviously not the one
that includes multiple incomplete files in a single playlist) without
needing any complex configuration options. An option in the context menu
for "stop without updating resume point" or possibly "return to resume
point" for cases when a file is accidentally opened, or the user
accidentally seeks might benefit as well.
I just feel this feature is very complicated in terms of offered options
for a feature that should be relatively simple and intuitive. It feels
engineered toward what I see as a fringe use case, rather than being a
significant convenience feature for most users. It's the sort of thing
that shouldn't need to be turned on, but rather "just work" while
simultaneously "not get in the way".