> well as an old high-end stereo (I'll need some digital-to-analog adapter, but I assume those exist). Those adapters exist, look into Airplay 2 compatible dev

> well as an old high-end stereo (I'll need some digital-to-analog adapter, but I assume those exist). Those adapters exist, look into Airplay 2 compatible devices. iTunes is pretty easy to use, my older parents don't seem to have much of an issue with it. Admittedly, I don't regularly use iTunes anymore, only for the occasional iPod sync or restore. Once you have Apple's HomeSharing setup, it's really easy to play stuff on your apple devices. The Winamp 2 default skin was pretty basic. It had a stereo layout (play, stop, skip buttons), an equalizer, and a playlist. It was a great stand alone app. If you were just wanting a simple way to play stuff on one computer, it might be the better way to go.