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Not a solution but you can set itunes to allow you to manually manage your music, so then you can simply drag/drop onto the device.
For Meta information, are you talking when ripping from CD's or do you have untagged MP3's in folders?

You're stuck with itunes though for apps, could you use something like foobar etc to organise then use itunes to sync?
 
What's wrong with the way it organises and syncs your music? There are several options, I would be very supprised if one of them is not suitable for you?

If you are going to getting an iPhone then iTunes is the only way for applications.

I don't have an issue with iTunes myself and use it for all my apple devices.

TrUz
 
You can disable itunes automatically looking it up, I think if you're importing cds etc. you get a pop up prompting you what album it is perhaps.
 
can winamp do ipods or is that a gimick remember it saying it could, dunno if thats the free version through.
 
Winamp works perfectly with iPods. BUT it syncs (you right click and "send" to the iPod) so not what you're looking for.

It's my weapon of choice though :)
 
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