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Babe project - Legal feedback


I'd like to discuss something with the community, and maybe get some legal input:

As some of you might already know I'm working on a open online platform to share music information between users, such as public playlists, comments on tracks and on the playback progress like soundcloud, share popular music suggestions, metadata, and discovery of new music from another users with integration with YouTube and Spotify etc... the platform will be integrated into Babe music player and could be use in any other music player

The legal matter comes here:
1- I would like to either have the option to *stream live* the music an user is currently listening to to a group of friends. here the music file isn't being storaged in the audience computer...
How ilegal is it? How illegal is to stream live, but privately, copyrighted music?  and how illegal is it to stream owns music content to a selected group of friends?

2- If the stream part wouldn't be enought problem, I'd also like to sync a user playlist marked as public to some other friends, that would mean to share music files between users, and technically downloading another users music files. How illegal is this part? how illegal is to share a music file for example, in a conversation in telegram or whatsapp, or even how illegal is it to send a mp3 to a friend over an email or even over google drive?

I'd like to get feedback about this issues.

As the project is going to be hosted by the KDE community this streaming part won't be implemented to avoid legal issues, but however I would like to have this discussion to get as many feedback as possible.

Thank you.