For me, shoutcast was always the prefered option, its widley supported and works really well...
I'm not sure if passing audio metadata like Artist/Title through analog would work at all...
Shoutcast was made by Nullsoft, the same people who make Winamp... so they work together. Winamp will ask you for the shoutcast server IP in which to connect to, so all you have to do is give it the IP/PORT number that shoutcast is running on your ubuntu box and Winamp should be able to connect from your Windows machine... all meta data about your playlist will be sent to the server this way.
There are other players out there that come with a shoutcast plugin - but I think Winamp is the best to use considering it was made by the same team as the Shoutcast server.
... having said that, OtsJuke DJ was the ultimate DJ Booth for Internet Radio, sadly it isn't free though.