Hey,
I searched and searched and couldn't come up with something similar. Is it possible to assign to each song (let's say in shuffle mode) more than one track that can play afterwards? Like a shuffle mode...but with a given range of possibilities (pre-decided)...just thinking aloud here. Maybe even create cues for each, so that, for example, if the beginning of a song is not suitable to follow immediately after the previous ending, you can pre-edit it. You would end up with a playlist with a certain range of indetermination but different from a shuffle, and the criteria wouldn't be that of 'most heard', or 'similar in style'...you pick it.
I hope I made myself understood...
Happy new year everyone!