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I just notice something in regards to what MrSinatra said about Winamp informing about missing files
If I have on a playlist such extension-less file but remove it from the drive before it gets played, then what happens? Winamp simply skips it. So a theory stating that Winamp stops at such files because it is suppose to signal in that way a missing file is plain wrong. And that is because also this happens with every other removed file- it gets skipped. That is except for e.g. TTA, because the plugin governing playback of that format [TTA Audio Decoder 3.5] spits an error box for a missing file
And so we have now a duality: Winamp allows plugins to decide what to do with missing files- but when it is a file not associated with a plugin then it takes control over it and by default [in version 5.8 on Windows 10] decides to stop playback. For me personally this is ridiculous approach- especially that it was not like it in 5.666 on Windows 7
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