Sync'ing from laptop to devices, via anything but iCloud, has gotten so much worse than it used to be. It used to be pretty good -- for it's time anyway. The ecology just isn't built for actual owned media anymore. And so many people have only a phone now, so no reason to try to sync. I think this is probably true on Android too. I don't know about the Watch, or what the documented ways are to get media files on it.…
> so many people have only a phone now, so no reason to try to sync. Wait until the AR glasses come out. I pretty much guarantee that media syncing will be a huge deal, and Apple had better get their iCloud act together by then. iCloud is a shambles; and I say this as an Apple user for more than thirty years, and has pegged his career to Apple.
This is one of those things that will hopefully be opened up with more standardization. There's nobody to blame but ourselves for not enforcing this earlier, and hopefully in the future opening an MP3 file won't be harder than it was in 2005.