close itunes and use it only when updating your ipod. then, go to winamp.com, dl and install their latest version. make use of their global hotkeys, awesome skinning and customization options, windshade modes to keep it on top of everything else while still being small and out of the way (for easy access to controls, etc), and a huge assortment of other gadgets and what not. they even have an add-on that allows you to update your ipod directly from the media library. and you can copy songs from any ipod to your harddrive (as if ripping a cd).

as for the keys, i dont really know if theres a good way to do that. since theyre macro keys and function only on your most current window youd have to do some crazy setup between it and whatever program you use to send keystrokes to your background accounts.