I don't know if I'd say its a mess. There are three options that are well aligned with emerging trends: Plex, Emby, and MythTV (to a lesser extent). The rest have a lot of catching up to do if they want to remain relevant.
Our client sought outside legal advice concerning topics of DRM and copyright (we are scientists and engineers, not lawyers). In general, it is illegal to stream copyrighted content (even if you own it) to devices that are not authorized to view the content. The results of American Broadcasting Cos. vs. Aereo, Inc (2014) make it quite clear these statements extends to services that re-broadcast over the air television in a public fashion.