SkyAmp can now generate a WinAmp playlist with a specified minimum duration, which is generated according to the settings of the configuration you make. However, a lot is dependent on the correct tagging of the songs! If a song hasn't been tagged with artist and/or album, it's considered a 'stand-alone' song, which means that another song of the same album can be inserted right after it.
SkyAmp now includes an interface to tag all songs in a certain directory with a specified artist and album-name, but routines to 'validate' the tagging as recorded in the database are still lacking. As a stop-gap measure, I could consider the directory the song resides in as the album. What do you think?