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auto-backups with a button to "re-instate" them (in prefs maybe?) sounds like a good plan to me, and similar to the idea of doing the same for the ML and history DBs that has floated around for some time.
it doesn't address the root cause, but it certainly would make the problem less profound.
EDIT: making the backups sounds like a good job for winamp agent, since its a separate process, and far less complex than winamp itself. it could monitor the files, and back them up say 30 seconds after a last change.
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