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While I don’t have a third party app to suggest, I wanted to let you know the following:
If you already have your personal music on your iPhone in the music app (or: you imported the mp3 files via iTunes or purchased them through iTunes) you can go to the watch app -> music -> add music… and select which albums should be stored on your watch.
You probably already knew this but if you didn’t you should give it a try.
This is the way.
Marco has put so much work into the Overcast watchOS app, yet it’s still flakey at times. I don’t think there’s anyone else that can be bothered dealing with all the hassle!
That was my guess too!
What’s wrong with the built in music app? It does exactly what you are asking for, with or without an Apple Music or iTunes Match subscription
I’ve found sync to be weird for my own uploaded music, and from what I remember (I’ve been an Apple Music subscriber for a long time now), the app was constantly trying to upsell you if you didn’t have a subscription.
One of the reasons I’d want to use something else is I want a lot less functionality.
I also think it’s a bit alarming, ecosystem wise, that there’s literally only one music player and it’s the one offered by the platform owner.