It's never ever happened with me but it can and has happened at times with other Winamp users, but never to the degree that was stated in whatever article/post you quoted above from Hydrogenaudio, where it said, "Most of the time, not always, winamp behaves as such"
That's just not true, else there would be craploads of posters flooding these forums and there have been relatively few. Whoever posted that at Hydrogenaudio probably has this problem as an individual (or as part of a minority), and should not have stated what was stated.
In any event, ther's an easy fix if it ever does happen... use VBRfix
in case you need to repair MP3s with messed up headers to get them to play properly in Winamp, and to also display the correct song length times.
More on VBRfix and ID3v2 tagging here