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".

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