Wow. Just found an awesome trick in iTunes. The fact that I've been using it for, what, close to a decade and have not known this (and the lack of it has PISSED ME OFF) is just WRONG. So many of you may have already known this, but for those that don't, here you go.
I've always had trouble with the lack of multiple condition lists. IOW, combining AND and OR (any) type lists. My solution was to create base lists and then do the OR part in a secondary list or something. The problem is that iCloud does not support nested lists. So probably 3/5ths of my lists don't sync. So I was browsing today and found a clip of someone using iTunes. there was a condition, "Any" in the left hand column and then sub-criteria. Here's an example: I want Yes, Porcupine Tree and Elvis Costello in a list, but only if the media kind is Music and the rating is greater than 2. So I create the "Any" type list with those artists. Then create another list that is AND: Must be in (the base playlist) and be Music and Rating > 2. Worked, but not in iCloud.
So here's the answer: Option-click on the + for iTunes rules. You'll add a sub-condition, not just a condition. So in my previous example, I create an AND list: rating > 2, media = music, and SUB CONDITION, ANY of the following are true: artist is Yes, Porc or Elvis. Works like a freakin charm and was instantly available in the cloud.
Dungeons and dragons UI, if you ask me.