I have an iPhone and I am SICK TO DEATH of trying to use iTunes. I want to throw my computer out of the window. So, I would like to jailbreak my iphone so that I can use some sort of other software to upload the huge amounts of music I have and NOT have to convert to iTunes.

So my question to you all dear readers is:
(1) if I jailbreak my phone, will I be able to use other software on it?
(2) if yes, how do I do it?
(3) what's the best software for using with a jailbroken phone
(4) how can I then sync my iPhone with my work Outlook calendar (which is what I originally ended up using iTunes for
(5) what software will ensure that I can keep my music on a portable external hard drive and not throw a hissy fit?

Okies. Thank you all for your help in advance!