Sounds like it would need to be done with a VBA script by putting all of the songfile names into a collection. Have a random function choose one of the songs and then have that item deleted from the collection after it has been played. As far as fading them and other stuff I would need to do some research on it to see how that is done.

You mention that you have a mountain of things you want to do with VBA most likely being a large part of accomplishing these advanced things do you want to go down this road. I can get you started with a code but will need the names of sound files. It will take some time to write out and I may not be able to effectively get to it till the weekend. Someone like John Wilson could probably bust it out in 30 minutes right away. lol Im not that good but I am happy to help. If anybody can do it faster go for it like I said I may not be able to get to it until the weekend.

Let me know.

Thanks