Could someone suggest the solution that is easiest for highly non-technical users? I'm talking about users for whom Netflix is too difficult and YouTube crosses that threshold if anything goes wrong. (And don't criticize the users, criticize your UI.)

I don't care how proprietary it is or who runs it, as long as they can use it. I am arranging to have their CDs ripped (they don't use the CD player and saw me using my music library - which is just files in the file system and VLC - and liked the idea of hearing their long-unheard, beloved music) and need something they can actually use. Otherwise, they won't get to listen to their music.

All they need to do is select a track and play it. No other UI needed; it will only confuse things.

In fact, something that handles ripped music and new downloads and streaming would be optimal.

I'm working on mStream which is a server that aims to be as simple as possible to setup and run

https://github.com/IrosTheBeggar/mStream

Its slow progress development wise. Making this easy takes a lot of time. Currently the sever is in good condition but it desperately needs a mobile app

That's very cool. For my purposes, I'm less concerned with the server-side; I'm kinda hoping to put the music in the cloud somewhere and outsource server administration. In any case, these users are in no way going to be setting up server themselves. They don't know what "server" means and don't use the word in sentences.

https://github.com/fatedier/frp

With this mstream server could automatically tunnel through a cloud service that gives them a domain and SSL certs.

This way I dont have to pay to host any of the users files on the cloud. All I need is a unlimited bandwidth vps to do the tunneling. And the user doesn't need to know what a server is, they just need to be able to run mStream.

I actually made a proof of concept which worked well. I just couldn't justify scaling it until I get a mobile app finished.