The easiest way to license your Shoutcast server in the USA and allow you to maybe make money streaming ads (many other licensing companies in the use does not allow this or if they do you'll pay a heavy price. But starting at $22.50/MO head to http://startinternetradio.tk
and if you want to have a cheap shoutcast server go to http://1000slots.tk
as you can have 1000 listener slots for just $19.95/Month on a dedicated Shoutcast server. Those who sign up for the server during the promotion are grandfathered because the usual price for say 100 listeners is $125/Month. So I'd suggest to get the server NOW.
Broadcasting software: I'd recommend SAM for the PC. The price is $300 but there is a payment plan available through the author's Web site http://spacialaudio.com
If you want to start a hobo Radio you could try a FREEware broadcast automation program called http://radiodj.ro
and B.U.T.T for the encoder. B.U.T.T takes time to configure to your player so that the Artist/Title/Song is properly displayed to the listener but with a few tweaks you can usually get B.U.T.T running but you'll also need to use the Stereo Mix for the sound recording so that it pipes to B.U.T.T correctly.
I've not messed with Winamp's New DSP since Shoutcast V2 came out but their older DSP works better with version 1.98 which a lot of shoutcast hosts still use and still works without failure.
Hope this helps you get off the ground.