WinAmp has shuffle features that prevent this problem. There are options
to "Do not repeat the same artist in a row" and "Do not repeat the same
song title in a row". There are other options that really make the
Shuffle feature great to use. It's unf...
I have exactly this same problem and also in my case it plays the
playlist and then gets to a track and starts repeating that track over
and over without shuffling to the next track.