Background: I'm abandoning OS X for Linux and I've been totally dependent on iTunes for over a decade (since I abandoned Windows for OS X!). My absolute must-have features, which iTunes and an OS-X-plus-Android app known as iSyncr provide are:
- Nestable smart playlists: e.g., I can make a smart playlist (perhaps from 3 'dumb' playlists and some criteria), and then I can make smart playlists which contain other smart playlists. I've used this, along with song ratings, to craft my own genre-based "biased shuffle" playlists that make sure I get the most out of my music - I hear the songs I want to hear once a year about once a year, and those I want to hear once a week about once a week.
- Sync to Android devices including play counts, last-played and last-skipped times. My smart playlists include criteria based on play count and last-played/last-skipped times, so playing and skipping songs on the Android device must update this data in the player software. iSyncr provides that bridge for me with iTunes.
It would also be extremely nice to be able to import this data from iTunes. It'd be really nice if the software were cross-platform, not Linux-only, so I can avoid more painful migrations in the future.
The last time I searched for something like this was about 5 years ago and nothing even came close. Has the landscape changed, or am I gonna be running iTunes in a VM? :(