Another +1 for Plex. I've got it running on a server in my basement, and I use it to stream content to the WDTV player, and I've used the Android app with my Chromecast as well. I've experimented with the iOS app on my wife's iPad as well, but haven't used it to watch anything yet. Everything works flawlessly.
A downside of Plex is, at least if you host it on a Windows box, you need to be logged in to the computer/server in order for Plex to stay running. If you log off, Plex closes. I don't know if they've changed it since, but someone developed a third-party wrapper that runs it as a Windows Service. I put that on my Windows server, problem solved.
I haven't paid anything for Plex, aside from a few bucks that I paid for the mobile apps. And if you really want to run it for $0.00, you can also hook up a laptop to the TV (or a HTPC, or anything with a web browser), and navigate to the web interface on your Plex server. Streaming via the web interface is free.
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