Shoutcast, Winamp, Joomla - how to tutorial

I have am looking to build my own online radio station. I have hosting and i want you to skype with me and teach me how to do the work. if you dont want to skype then you will need to create a very detailed how-to-video or how-to-article explaining the process for me to complete the job myself. i want to build a few radio station so i need to understand the process. i am working with a pc, and windows xp. i have filezilla and i know how to create a data base and build a joomla website. but i am having a hrd time understanding what i need to complete my radio show. here is an example of a website design that i would be happy with. [login to view URL] see how each channel plays different music and has it's own pop out player. this is what i am looking for. i also want to know how to put my station on itunes. after the website is launced. **** the radio channel should pull files from my database and play them randomly. i want it set up so it can run weeks without maintenance.. i have looked into buying and using this software - [login to view URL] but i understand there are others out there and i am really open to doing whatever works. tell me what i need, tell me what you think but whatever you tell me make sure you have examples or refrences to make me a believer