> Rocket Player - paid a few dollars for it near a decade ago and it's still decent.

I would have +1'd that – the combo of iSyncr + Rocket Player was perfect for transitioning from iTunes + iPod to iTunes + Android phone while keeping bi-directional syncing of play counts and ratings intact. Rocket Player also supports smart playlists, which is also nice, even if you cannot sync those directly with iTunes and need to manually re-create them on your phone again.

(iTunes has its foibles, but on the other hand I don't find it that terrible, either, and at that time it was the only workable solution I found for bi-directional syncing of ratings and play counts between computer and phone. Plus while I appreciate that with Android you can just copy files directly to your phone and be done with it, a dedicated syncing solution also has its advantages – I don't have to remember to manually copy a file over each time I edit its metadata in any way, and I don't have to setup a ton of exclusion rules like I would have to if I wanted to sync my computer's Music folder with a regular file syncing software.)

Plus Rocket Player has some dedicated support for podcasts synced over from iTunes – since unlike my former iPod my phone has direct internet access, I'd be happy to just use a separate podcasts app for listening to actual podcasts without having to go through iTunes, however I've also been manually adding files as podcasts in iTunes because I've found that to work quite nicely for managing my collection of radio comedy show episodes scrounged together from all corners of the internet. Rocket Player puts those in a separate Podcasts section apart from the rest of my music library, shows which episodes have been listened to, and remember the playback position (and can even sync that with iTunes).

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Except – the original developer of Rocket Player and iSyncr sold his apps not that long ago, and it seems like the new owners are mostly only interested in extracting as much money as possible (supposedly changing both apps from one-time payments for the non-trial version into ridiculously overpriced monthly subscriptions) while doing as little work as feasible before the whole thing completely crashes and burns. So the whole thing (last app version before the sale) might or might not stop working once I have to switch to a phone with a newer Android version (Google isn't as bad as Apple on backwards compatibility, but it's no Microsoft, either), and I've got no idea what to do then…

Supposedly MusicBee (for your PC) allows play count/ratings syncing with either PowerAmp or Gone Mad Music Player, though I haven't tried it myself yet and with newer Android versions you might have to compile the sync app yourself because it hasn't been rewritten for Google's ridiculously over-complicated new file access permissions system.

Supposedly at least Gone Mad also supports smart playlists, too (PowerAmp on the other hand looks like it doesn't?), so if I had to switch, I suppose that's what I'd switch to.

Unfortunately it seems there is no good replacement for iTunes + Rocket Player's podcast handling – while MusicBee imports your iTunes library (with mixed success as far as podcasts are concerned), it doesn't allow manually adding files as podcasts (and on a Mac even Apple itself has broken things, because post-iTunes-split-up the new separate Podcasts app no longer allows manually adding files, either), and on the Android side I suppose things don't loo much better, either. I suppose I might have to set-up a fake local podcasts server on my computer and switch my collection of radio comedy over to my dedicated podcast player app on my phone…