Apart from winamp(which doesn't auto refresh the contents of my ipod after file transfers) is there any other (free)software that can I can use to transfer music to my ipod?

I don't think there is.

The main issue with iTunes alternatives is no other place has all the music

Apple are fussy with what you can connect to your iPod, so I think iTunes is the only way

nvm

Winamp will do it, but it's me being fussy and wanting the contents of the 'pod to visibly update when I drag new music on to it.

Argh!! I just updated winamp and now it won't let me drag music from windows explorer onto my pod!

BOO! Updates suck.

MediaMonkey?

Seriously, no matter how shit iTunes is, it's the best out there unless you wanna spend about $20 on a plugin for WMP.

The problem is I don't want to use a library, I just want to drag and drop from windows.

@ mistershine, you can use a programme called total commander to transfer stuff to iPods, though I am not sure entirely where I got it from

Well I think that's impossible.. I use a mac and from what I know an Ipod has his own disk mode so you can't easily acces the MP3 files..