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I haven't used it in a while but I would probably try shoutcast w/ winamp. I know they have a linux version of the server. I am not sure if its free, but last I used it is was for non-commercial use.
icecast with winamp.
Assuming the songs are in the VPS... no Winamp ¬¬
@yomero, Yes, I'll keep all files in my VPS and just play those one by one and continuously. So what may help me when I don't have whmsonic/autodj?
I haven't played too much with icecast. What I've used is VLC n_n
Probably isn't the easier one :P (IIRC "ices" is good too :P )
Something like ices+icecast would be good for pure CLI. You could install Airtime, which is a free radio station web manager.. thing. Could be pretty weighty, though.
Are you expecting to have an audience, or are you trying to listen to your music from multiple locations or on the go?
@Damian, I'll use that for people who can listen some selected songs from our website.
Red 5? http://www.red5.org/features/
Subsonic