Good day all, I did a lot of searching last night and couldn't find a solution so I just wanted to put this out there in case someone else is in my situation.

That is, in order to send music/video to your XBOX 360 from Windows 8 it must be on the same ROUTER (this could be the subnet and is most likely broadcast related but I'll try and keep it simple).

In my home I have a router to my Internet provider (Verizon FiOS) and another router at my desk. The router at my desk is purely to make it easy to plug multiple devices in. The first time I sent video to my 360 using 8 it worked great, the next time it didn't.

The difference was the first time I was connected wirelessly into the same router the 360 is connected to, the second time I was using a cable into my daisy chained router.

After a bit of searching, frustration and hair pulling I finally realized what the problem was, took out the cable, connected wirelessly and could then see the 360 and send video/music to it.

Summary (for Google searchers)

Send to 360 must have the "sending system" on the same router as the XBOX 360.

Hope this helps someone at some point in the future.