In my experience, the middle setting in AC results in a file about the size of a 128k fixed file. Not quite the same, but close.
I encode most of my albums at this bitrate and I'm quite happy with them. For those extra special ones (i.e., remastered versions of Moving Pictures and Hemispheres), I crank it all the way to the top and it still compresses pretty good.
I have no idea what your WinAmp problem is. I could give you Justin Frankel's home phone number and you could ask him... (Just kidding).
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Tony Fabris