Sam,
It sound like you are about to pull hairs out attempting to complete a "Smartlist". I predicted it would be forever time consuming for me, so I didn't bother to start a "Smartlist". The bigger your music library the worst it is to create list that i feel should come right out of the box on day 1. At least that's the way the old MixVibes did it.
I posted a request in the Request area,
viewtopic.php?f=360&t=40353 .
Any DJ software needs to be able to sort Tags right out of the box, I shouldn't have to generate trivial groups of my music library.