Quod Libet is cross platform and runs on my Ubuntu box, Windows Surface and MacBook Pro. It is fast, has a simple interface that actually works and has been extremely stable. It also manages playlists that work in my car's USB port. I do like having my music in the cloud, and finally settled on Dropbox. I am still looking for a decent Android Dropbox music player for this setup, but for iOS, I use Eddy cloud music player/streamer. It even bookmarks my place in audio books. Sad part about Eddy is that it takes so long processing my entire music library on Dropbox and starts the whole process over when reinstalled. Also, haven't figured out how to get it to work with playlists saved to Dropbox, but I have asked for the feature.

It was Apple's changes to the music app on my iPhone that finally annoyed me enough to seek an alternative setup which baffles me, because the only reason I was convinced to ever purchase my first Apple product was an iPod and they have completely screwed it up.

I did use Google Music, but Google's insistence that the desktop doesn't exist made it useless on Windows & Mac. I tried every Google Music app I could find for either platform. They are unstable, often slow, and usually break every time there is an API change.

In a similar vein, is there a general recommendation for locally web hosting your music yourself. Is it one of the plexy type setups?

More OT, but what about personal photos / videos? I find the whole Apple photos experience depressing. Two examples of why

- my wife and I really share a photo collection, but it's neigh on impossible for us to automatically sync all our images to one another

- this weekend I made a stop motion clip with my kids by taking photos on my phone. We tried to move the images to my computer so we could put them together / edit them but were stuck waiting for the devices to sync on some sort of black magic driven schedule.

Is there any general solution out there for families who want to share their content (local music collection and photos / videos taken) seamlessly?

There isn't a good one, because iTunes sucked all the oxygen out of the room. I gave up. I use VLC to play single files (no library), and I have a separate Sonos system with its own speakers and amp for my library.

Have you tried Clementine? https://www.clementine-player.org

Vox is not perfect but works fine as a player: http://coppertino.com/vox/mac

On OSX I quit and just use preview. I'm not even kidding.

For just playing mp3s, I like https://cmus.github.io/

Open cubic player might have OSX support (OSX has OSS right?)

Is it a mess? Yes, but it's not really bloated.