Ok cool.. see thats weird though, cuz Artwork#2 was definitely on top of Game List 
Anyway, as far as ordering, heres the last 3 items out of a .lay file.. I assume these are a static order, and they seem to be in the same order as whats in the Display Objects/Main Form list
False
 0 
 8421504 
 16777215 
System
True
False
 9.75 
 2 
 90 
 0 
 640 
 430 
True
 1 
 0 
 13408512 
System
True
False
 9.75 
 2 
 0 
 558 
 800 
 20 
True
 1 
 0 
 16777215 
System
True
False
 9.75 
 2 
 0 
 580 
 799 
 20 
Now I may not have the right break points but it should be close to this.. What if when it wrote the .lay file, it added tags
[Game List]
False
 0 
 8421504 
 16777215 
System
True
False
 9.75 
 2 
 90 
 0 
 640 
 430 
[Artwork #1]
True
 1 
 0 
 13408512 
System
True
False
 9.75 
 2 
 0 
 558 
 800 
 20 
[Artwork #2]
True
 1 
 0 
 16777215 
System
True
False
 9.75 
 2 
 0 
 580 
 799 
 20 
I dont know how hard this would be or what youre capable of, but what about a dialog like this, instead of the list with checks thats currently there:

(thats from the column select in outlook express) When saved, it could just write the file in the order of that list, and when it's rendered, it could use the tags- for example in that second bit, GameList would be drawn, then Artwork#1, then #2
Anyway just kickin around thoughts.. I was monkeying around with it and different skins for different emu's last night and I'm likin' it