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I think most of your problem as described above is down to trying to start a new instance of Winamp, before the old one has closed properly.
It can take quite a while sometimes for Winamp to close, and a new instance wont be able to get under way until the file handles are released from the old one.
I've seen something like you describe at first launch. but generally being too hasty starting an mp3 after closing Winamp gives an error here - 'The interface is unknown'.
UJ
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