I've waded through the profusion of "iTunes on Linux" questions on this site and the recommendations (as well as searching Google extensively) but have not seen the combination of features that are important to me.
The keynotes that I see missing (or at least don't see advertised) from most candidates are:
- Excellent support for playlist syncing to Android
- Arbitrarily nested playlists/folders
- Support for audiobooks (which are split into multiple files)
- Support for videos and organization thereof (including multi-gigabyte full movie files)
Also, one other thing that I'm not sure exists anywhere (it doesn't really exist in iTunes): organizational features that apply well to a lecture series. (These features would likely apply as well to an audiobook of sequential short stories, if that helps to conceive of it.) On iTunes I make do with calling the whole lecture series "one audiobook" and then creating playlists in a folder to contain individual lectures within the series.
The app must not require me to upload all my files, so Google Play is out. I want control of my files.
Open source would be really nice but is not mandatory. Open file formats for the playlists and any other metadata is mandatory.
The closest I have found so far is Quod Libet, which doesn't appear to support syncing with Android, but looks to have extremely good playlist/organizational capabilities.